摘要:

1310 PERKIN AND HORSFALL: GENISTEIN. PART 11. CXXV. -Genistein. Part 11. By ARTHUR GEORGE PERKIN, F.R.S.E., and LOUIS HUBERT HORSFALL. IT was shown (Trans., 1899, ’75, 830) that dyer’s broom (Genista tinctoria) contains, in addition t o luteolin, a new substance genistein, which possesses feeble dyeing properties. When decomposed, the latter gave phloroglucinol and an acid resembling p-hydroxyphenylacetic acid, and this reaction, together with its other properties, indicated i t t o be a trihydroxyphenylketocumaran. 0 Further investigation, however, was desirable in order t o establish the identity of the acid and the nature of the products of methylation. These points could not be dealt with previously owing to the small quantity of genistein which the plant contains and the laborious nature of the operations for its extraction and complete purification. For the apparently meagre results of this paper, 25 grams of genistein were employed, the preparation of which extended throughout five months.Methylation products of Genistein. It has been shown (Zoc. cit.) t h a t by methylation genistein yields t w o dimethyl ethers, (a) the main product melting at 13’7--139O, and ( b ) present in minute quantity and characterised by its sparing solubility in alcohol. This substance, to which the formula C1,H80,(O*CH,), was assigned, yielded a monoacetyl compound, C,,H70,(0*CH,),* C,H,O, and that the latter had t h e composition assigned to i t was evident from a study of its decomposition with an acid. The ether (a) was first examined.PERKIN AND HORSFALL: GENISTEIN.PART 11. 1311 0.6710 dissolved in 15 C.C. of boiling acetic acid and treated with 2 C.C. of sulphuric acid gave 0,5815 C,,H,,O,. Found 86.66 per cent, Calculated S7-19 per cent. Decomposition w i t h AZcoholic Potaslb.-The dimethyl ether ( a ) was digested with strong alcoholic potash a t 150-160O for 3 hours. The resulting solution was evaporated to dryness, the residue dissolved in water, neutralised with acid, treated with excess of sodium hydro- gen carbonate, and extracted with ether. On evaporation, a small quantity of colourless residue remained which did not crystallise on long standing, and was similar in character to that yielded by luteolin trimethyl ether (this vol., p. 1317) by this method. To identify it, the residue mas dissolved in dilute sodium carbonate solution, diazo- benzene sulphate added, and the red precipitate thus produced collected, washed, dried, and purified by extraction with alcohol and crystal- lisation from a mixture of alcohol and acetic acid, It formed a glisten- ing mass of orange-red needles melting a t 251-252', did not dissolve in cold aqueous alkalis, and was identical with disaxobenxenephloi.o- glucinol mononzethyl ether, previously prepared from the methyl ethers of quercetin (Proc., 1900,16, 1Sl) and luteolin.The sodium hydrogen carbonate solution from which this phenol had been removed mas neutralised with acid, extracted with ether, and the extract evapor- ated. The resulting oily residue gradually solidified and mas then digested with boiling light petroleum, filtered, and the crystals which had separated overnight recrystallised from the same solvent with the aid of animal charcoal.0.1088 gave 0.2594 CO, and 0.0595 H,O. 0.1365 ,, 0,1940 AgI. CH,=9*07. C = 65.02 ; I1 = 6.07. C,H,,O, requires C = 65.06 ; H = 6-02 ; CH, = 9.03 per cent. This acid consisted of colourless leaflets melting a t 85-S6', and was identical with the methoxyphenylacetic acid, CH,*O*C,H,* CH; CO,H, prepared by Cannizzaro (Annulen, 1861, 117,243). The decomposition products of genistein dimethyl ether ( a ) are thus phloroglucinol mono- methyl et?Ler and p-methoxyphenylacetic m i d , consequently this com- pound is the nornzd dimethyl ether of the colouring matter. The sparingly soluble Dinzethyl Ethw @).-The yield of this product was exceedingly small and little more than one gram was available for investigation.The melting point, previously given as 1 87-189", is foo lorn, and should be 200-202°. I t has been shown (loc. cit.) that this substance contains two methoxy-groups, and that by the action of hydriodic acid genistein or a very similar compound is formed. To account for its production, it seemed possible that during methylation a methyl group had entered the ring, the product being consequently a dimethyl ether of methylgeiiistein (loc. cit.). 4 u 21312 PERKIN AND HORSFALL : (XENISTEIN. PART 11. The acetyl derivative prepared in the usual manner forms colourless It needles, dissolves sparingly in alcohol, and melts a t 212-214O. contains only one acetyl group. 0.6548 gave 0.5768 regenerated ether.Found 88.08. CI4H70,(0*CH3),* C,H,O requires Cl6HI4O5 = 87.1 9 per cent. CH,* G14H603(0*CH3)2* C2H30 ,, C&,,O, = 87.72 ,, The regenerated dimethyl ether melting at 200-202° was 0.1148 gave 0.2886 GO, and 0.0555 H,O. By the action of alcoholic potash at 150-160°, this ether yielded a n acid which crystallised in colourless leaflets, melted at 85-86', and was identical with p-methoxyphenyhcetic acid. The phenolic pro- duct of the decomposition became crystalline on standing, and was identical in appearance with that yielded by the analogous trimethyl ether of high melting point from luteolin (Zoc. cit.). That it was the same substance was confirmed by the preparation of its disazobenzene derivative, for this formed orange-red needles melting at 198-2019 As previously indicated, this is most probably disaxo6enxenernethdyZ- phloroglucinol monomethyl ether, and consequently the ether obtained from genistein melting at 200-202° is considered to be rnethylgenistein dimethyl ether.anal y sed. C=68.56 ; H=5*37. C17H,,0, requires C = 68.00 ; H = 5.33 per cent, The following would appear t o be its constitution : 0 To determine whether any characteristic distinction could be noted between genistein and the presumed methylgenistein, a trace of each was prepared by the decomposition of the respective methyl ethers with hydriodic acid. I n appearance and general reactiocs, both pro- ducts appeared to be identical, but a distinction in the melting point was'noted, as the genistein melted at 287-289',* and tho methylgenistein at 276-27S0.From these results, it is unlikely that methylgenistein or its glucoside exists in the Genista tinctoria, and the substance is almost certainly produced in the form of its ether during methylation. Owing to lack of material, experiments could not be made t o determine if it could be formed by digesting genistein dimethyl ether with methyl alcoholic potash and methyl * A sample of genistein from the dyer's broom, the purity of which could not be doubted, melted a t 291-293", slightly higher than that from the ether, a fact readily explained, as the quantity of the latter did not admit of recrystallisation.PERKIN AND HORSFALL: GENTSTEIN. PART 11. 1313 iodide, but by acting a t first with a somewhat larger quantity of the alkali and iodide upon genistein, it was observed that the yield of tbe methylgenistein compound was somewhat increased.Owing to the difficulty in preparing it, we do not propose to examine it fur- ther, for i t s analogy to the rnethylluteolin ether is evident. Genistein Diethyl Ether. Genistein dissolved in a solution of potassium hydroxide (5 mols.) in ethyl alcohol was digested a t the boiling point with excess of ethyl iodide for 3 days. From the resulting solution, which on cooling formed a semi-opaque, gelatinous mass, unaltered ethyl iodide was removed by distillation; the alcoholic liquid was then poured into much ether, and the product washed with water and evaporated to dryness. The amorphous, horn-like mass was dissolved in boiling alcohol, allowed to partially cool, and a small quantity of an indefinitely crystalline substance ( c ) which separated, was rapidly removed by filtration through calico.This operation had for its ob- ject the removal of a less soluble ether if such should be present, as is the case with the methylation product. The filtrate became gelatin- ous on cooling, and as other solvents did not yield a crystalline pro- duct, it was evaporated to dryness and acetplated in the hope that the resulting compound would be easier to manipulate. This was found to be the case, for the nzonoacetyl derivative, Cl,H70,(0*C,H,),*C,H30, crystallised in colourless needles melting at 168-1 70". 0.1120 gave 0.2780 CO, and 0.0575 H,O. C,OH,oO, requires C = 67.41 ; H = 5.62 ; CI8Hl8O5 = 88.20 per cent. The genistein diethpl ether regenerated from the above substance could now be crystallised from alcohol, in which it is sparingly soluble, and was thus obtained in colourless needles melting a t 132-134'.The mother liquor should be removed while still warm, as the later separations are deposited in the gelatinous condition. C=67*68; H=5*70. 0.4165 ,, 0.3670 C18H180,. C,,H1,05 = 88.11. 0.1087 gave 0.2752 CO, and 0.0573 H,O. C=69*04 ; H=5.85. C18Hl,0, requires C = 68-79 ; H = 5.73 ; C,H, = 18.47 per cent. The ether was decomposed with alcoholic potash and the products separated in the same manner as those yielded by the dimethpl ether. The acid thus obtained formed colourless leaflets melted at 88", and had the properties of p-ethoxyphenylacetic acid, C,H,*O*C,H,*CH,*CO,H. C,oH120, requires C = 66-66 ; H = 6.66 per cent.0.0645 ,, 0.1005 AgI. C,H, = 19-22, 0.1051 gave 0.2546 CO, and 0.0593 H,O. C = 66.06 ; H = 6-27,1314 PERKIN AND HORSFALL: LUTEOLIN. PART 111. The accompanying phenol is most probably phloroglucinol mono- ethyl ether, but owing to lack of data this cannot yet be identified. When treated with disazobenzene sulphate in the usual manner, an orange-red compound resulted, which crystallised from alcohol in needles, and was insoluble in cold aqueous alkalis. The product (c) obtained during the purification of the above substance melted a t 127--129", and did not appear to contain a second ethyl ether, although, as a mere trace was available, it could not be properly examined. Experiments were carried out in the hope of preparing a pure azo- benzene derivative of genistein, but these, as well as those for 'the production of nitro-derivatives, were unsuccessful ; they indicated, however, that if sufficient material were available for the determin- ation of the necessary conditions, such derivatives could be produced, a s has been the case with the somewhat closely allied colouring matter apigenin.Szcmrnarg of Results. When methylated, genistein, like luteolin (Zoc. cit.), gives two ethers which are insoluble in aqueous alkalis, and capable of forming monoacetyl derivatives. That melting at 137-139" is the normal dimethoxy-compound, whereas the second, which melts a t 200-202", is considered to be methylgenistein dimethyl ether. It is probable that the formation of the latter is due t o a methyl group entering the ring of the phloroglucinol nucleus during methylation, for there is no evidence to show that methylgenistein (or its glucoside) is contained in Genistcl t i n c t o r i a . The production of p-methoxy- and p-ethoxy-phenylacetic acids from the corresponding ethers of gen istein proves that the acid previously obtained from this colouring matter is p-hydroxyphenylacetic acid; and the results, as a whole, are in har- mony with the constitution which was previously assigned to genistein. CLOTHWORKERS' RESEARCH LABORATORY, DYEING DEPARTMENT, YORKSHIRE COLLEGE,

ISSN:0368-1645    

DOI:10.1039/CT9007701310

出版商:RSC    

年代:1900

数据来源: RSC

摘要:

1314 PERKIN AND HORSFALL: LUTEOLIN. PART 111. CXXV I. - Lu t eolii A. Part 111. By ARTIIUR GEORGE PERKIN, F.R.S.E., and LOUIS HUBERT HORSFALL. IN previous communications (Trans., 1896, 69, 206, 799), it was shown t h a t luteolin has properties which harmonise with those of ‘a tetra- hydroxyflavone. The present work was undertaken t o support this contention arid to throw light on some obscure points which occur in these earlier investigations.PERKIN AND HORSFALL: LUTEOLIN. PART 111. 1315 It has been shown (loc. cit.) that the isolation of luteolin from weld, a t best a laborious task, is much simplified by the method devised by one of us, and this process has been again employed. An improve- ment is effected by adding a concentrated alcoholic solution of the very crude luteolin to ether, omitting the preliminary extraction with this solvent. After removing insoluble matter, the ethereal liquid is washed with water, evaporated t o dryness, and the yellow residue sub- mitted to purification.If for this purpose crystallisation from dilute alcohol is employed, and the mother liquors are worked up as far as possible, a small quantity of a product eventually remains which does not crystallise readily, and tends to gelatinise. As the bulk of this residue, unlike luteolin, gave no insoluble hydrobromide in the presence of acetic acid, this method could be employed for its isolation. The acetic acid filtrate from the luteolin hydrobromide was poured into water, the dull yellow precipitate collected, well washed with water, and dried. A solution of this product containing a trace of acetic acid was now treated with lead acetate solution so long as a precipitate formed, and this was filtered off and thoroughly washed with boiling alcohol.Tho filtrate, after evaporation t o a small bulk, was treated with a little boiling water, the semi-crystalline deposit collected, and further purified by crystallisation from alcohol. Exam- ination of the product by Zeisel's method proved the absence of a methoxy-group, but i t was observed that by the action of the hydr- iodic acid a purer substance was obtained. The main bulk was there- fore treated in this manner, and finally crystallised from dilute alcohol. 0*1082 gave 0.2617 CO, and 0.0389 H,O. C = 65.96 ; H= 3.99. 0.1156 ,, 0.2792 CO, ,, 0.0413 H,O.C = 65.87 ; H= 3.96. CI,HloO, requires C = 66.66 ; H = 3-70 per cent. The substance formed almost colourless leaflets, and when heated showed signs of melting a t 235', being completely liquid at 344'. With alcoholic lead acetahe solution, it is partially precipitated as a yellow lead compound, and with alcoholic ferric chloride a brown coloration was produced. It was readily distinguished from luteolin by its feeble dyeing properties. On fusion with caustic potash a t ZlO", the substance yielded phloro- glucinol (m. p. 210°), p-hydroxybensoic cccid (m. p. 209-210'), and traces of protocatechuic acid and a substance resembling p-hydroxyacetophenone. These results indicated that ic was apigenin, which exists as a glucoside in parsley, and as the glucoside of its methyl ether * in the leaves of * This apigenin niethyI ether, acacetin, seems to be identical with that recently prepared by Vongerichten, which contailis the methoxy-group in the 4'-position (Ber., 1900, 33, 2908) ; its examiiintion will be continued.1316 PERKIN AND HORSFALL: LUTEOLIN.PART 111. Robinia peudacacia (Trans., 1900, 77, 430). It has been shown by Vongerichten (Ber., 1900, 33, 2334) that the presence of proto- catechuic acid in the decomposition products of apigenin previously observed by himself (Ber., 1876, 9, 1124), and later by one of us (Trans., 1897, 71, SOS), is due to a contamination of the apigenin from parsley with luteolin monomethyl ether, and the reappearance of this acid here, as well as the slightly low analytical numbers given above, were evidence that our substance still contained a trace of luteolin.The remaining portion was therefore dissolved in alcohol, the solution treated with a little lead acetate, and the colouring matter recovered from the filtrate in the manner previously given. It now melted at 342-344', a temperature which nearly coincides with the melting point of synthetical apigenin (347") given by Cxajkowski, von Kos- tanecki, and Tambor (Bey., 1900, 33, 1992). To removeall doubt on the point, the substance (0.75 gram) was converted into its methyl ether, which crystallised in pale yellow needles melting a t 166-167O, and was evidently identical with the apigenin dimethyl ether pre- viously described. The percentage of apigenin in weld appears t o be very small, as the quantity of pure substance isolated for these experi- ments was only 1.5 grams from 31 lbs.of weld extract Owing, however, t o the fact that apigenin is partially precipitated by alcoholic lead acetate, it is obvious that the above does not represent the full amount present in the extract, MiethyZation of Luteolin. It has been shown (Zoc. cit.) that when methylated, luteolin yields an almost colourless substance melting at 191-192', which contains three methoxy-groups ; to this the formula CI5H6O6(CH3), was assigned. Subsequently, Herxig (Monatsh., 1896, 17,421) expressed the view that this substance was probably the trimethyl ether, C,,Ht0,(O*CH3),, and not a tetramethyl compound. As analytical numbers a trifle lower than those given a t first were afterwards obtained, this view of its composi- tion was adopted.The explanation previously suggested by one of us that a methyl group had entered the ring appeared also unlikely, judging from the behaviour of analogous colouring matters of the quercetin type ; moreover, the small yield amounting approximately to 7 per cent. from the exceedingly expensive luteolin, rendered its examination extremely difficult. After careful consideration and a fuller experience of this class OF substance, however, it was difficult to believe that this was the normal trimet.hy1 ether, C1,H70,(O*CH3)3, for its melting point was not only particularly high, but its crystalline property did not resemble that of the corresponding triethyl ether. Somewhat later (Trans., 1899, 75, 835), it was noted that genisteinPERKIN AND HOBSFALL: LUTEOLIN. PART 111.1317 when methylated forms two dimethoxy-compounds, one having, like the luteolin compound, a high melting point, whereas the second appeared to be the normal compound, The difficulties involved in the preparation of large quantities of genistein rendered the full examin- ation of its ether of high melting point practically impossible, but it appeared likely that its constitution could be settled by the investiga- tion of the seemingly analogous luteolin derivative. For this investigation 30 grams of luteolin were methylated in the manner already described* and 2.5 grams of the pure compound were obtained melting at 291-192O. With alcoholic potash, a potassium salt crystallising in fine yellow needles resulted, which mas decom- posed by water with regeneration of luteolin.Previous analyses (Zoc. cit.) gave C = 66.86 ; 66.92 ; H = 5.71, 5.58 per cent. 0,1278 gave 0,2596 AgI. CH, = 12.97. C16H90,(0*CH3)3 requires C = 66.66 ; H = 5.26 ; CH,= 13.17 per cent. The acetyl derivative was again prepared and melted at 175-176', a degree higher that previously stated. Analysis showed that it con- tained but one acetyl group. 0.5261 gave 0.4666 C,,H,,O,. Found 88.69. C,,H170,-C,H30 requires C,,H,,O, = 89.06 per cent. So far, therefore, the results accorded with those required by LZ Iuteolin trimethyl ether. It was now decomposed with alcoholic potash at 16OC, and the pro- ducts separated as described in connection with the triethyl ether (Zoc. cit.). An acid identified as ueratiic acid (m.p. 176-178') was thus obtained, together with a syrupy phenolic product, which on standing crystallised in slender needles. As the small quantity of the latter rendered its identification as such doubtful, its azobenzene derivative was examined, for in this manner it has been possible t o identify the phenolic decomposition products of rhamnazin and other ethers of this class (Perkin and Allison, Proc., 1900, 16, 181). Diazobenzene sulphate was added to a solution of the phenol in aqueous sodium carbonate, and the orange-red precipitate collected, washed, dried, and purified by crystallisation from alcohol. 0.0574 gave 7.9 C.C. nitrogen a t 20' and 748 mm. N = 15-49, C,H,O,(N,*C,H,), requires N = 15.47 per cent. The disazo-compound was obtained as a spongy mass of orange-red needles melting a t 198-201° and insoluble in cold aqueous alkalis.* The yield was not increased by redigesting the product of the reaction with further quantities of methyl alcoholic potash and methyl iodide.1318 PERKIN AND HORSFALL: LUTEOLIN. PART 111. From the results given below, it is evident that this compound is a phloroglucinol derivative ; i t is not, however, disazobenzenephloro- glucinol monomethyl ether (Zoc. cit.), or disazobenzenephlorogli~cinol itself (Trans., 1897, 73, SlS), for these substances melt respectively at 251-252O and 228-230O. From the temperature employed in the decomposition of the trimethyl ether, it is evident that the phenol from which it was derived contains a methoxy-group, and there is thus a strong probability that this compound is disazobenzenemethylphloro- glucinoZ monomethyl ether.Consequently, it is assumed that the methyl ether melting at 191-192O contains a methyl group in the phloro- glucinol nucleus, and is a rnethylluteolin trimethyl ethes-. It was interesting, therefore, t o examine the colouring matter pro- duced by the decomposition of this ether by means of hydriodic acid. The operation was carried out in the usual manner, the product crystallised from dilute alcohol, and extracted with boiling benzene t o remove unaltered ether if present. 0.1011 gave 0.2373 CO, and 0.0428 H,O. C = 64.00 ; H = 4-70, Cl6Hl2O6 requires C = 64.00 ; H = 4.00 per cent. The compound was obtained as glistening leaflets, identical in appear- ance and general reactions with luteolin itself.Fused with alkali, it yielded a substance having the phZorogluci.noZ reaction, but as a mere trace of the colouring matter was available for the experiment, this phenol could not be isolated in a pure condition. It has been shown that the trimethyl ether gives veratric acid ; thus the acid product of the above decomposition is potocatechuic acid. The acetyl compound of this colouring matter formed colourless needles, sparingly soluble in alcohol, and melted a t 239-240' when rapidly heated, and a t 235-236O when the operation was conducted slowly. This is considerably higher than the melting point of acetyl- luteolin found by us (222-225') or by Herzig (221-225'), and again distinguishes it from luteolin. The melting point of methylluteolin is apparently lower than that of luteolin (327-329O), and is provisionally given at 307-309'.As the trace available did not admit of recrystallisation, we leave the point undecided until a larger specimen is available, although this value is probably correct. More soluble Product of the Reaction.-It has been previously stated (Trans., 1897, 73, 191) that in addition to the above compound some quantity of a second is produced by the methylation of l u t e o h in the manner described. From the mother liquors emanating from the puri- fication of the ether of high melting point, this separated on complete cooling, and more was obtained on concentration. After preliminary crystallisations from alcohol, with the aid ofPERKIN AND HORSFALL: LUTEOLIN.PART III. 1319 animal charcoal to remove a brown impurity, the product was fraction- ally crystallised from benzene. A first deposit consisted of almost colourless, warty nodules of the ether of high melting point, but the main bulk separated in long needles containing benzene of crystallisa- tion, and these were collected apart, recrystallised from benzene, then repeatedly from mixtures of alcohol and other solvents, and finally from alcohol alone. Thus obtained, the product melted at 157-158", and was apparently pnre ; subsequently i t was observed that by the decomposition of its acetyl Compound, the regenerated substance melted a t 161-163". The tlificulty of obtaining the compound in this condition of purity was remarkable when compared with the comparative facility with which the analogous ethers of genistein are separated.Possibly a trace of the methylluteolin trimethyl ether of high melting point contaminated the product, although this seems t o be unlikely judging from the methods adopted. 0.1202 gave 0.2897 CO, and 0.0565 H,O. C=65*73; H=5*22. 0.1940 ,, 0.4180 AgI, CH,=13*75. Cl5H,O, (O*CH3), requires C = 65.85 ; H = 4.88 ; CH, = 13-78 per cent. This ether was obtained as glistening, lemon-yellow needles, some- what sparingly soluble in alcohol. With alcoholic potash, i t gives a bright yellow salt in the form of minute needles, soluble in 50 per cent. alcohol to form a pale yellow liquid, and is thus more stable i n the presence of water than the methyllutsolin compound. This was also evident from the fact that although luteolin trimethyl ether is in- soluble in aqueous alkali, it dissolves appreciably in a 50 per cent.alcoholic solution of potassium hydroxide. The monoacetyl compound, referred to above, formed colourless prisms readily soluble in alcohol and melted at 156--158'. 0.4536 gave 0.4038 C,,H,,O,. Found 89.02 per cent. C,,H,O,(O*CH,),* C,H,O requires C,,H,,O, = 88.65 per cent. On decomposition with alcoholic potash, the trimethyl ether gave uemtric acid, and a syrupy phloroglucinol derivative which did not crystallise on long standing. From the latter, an azobenzene derivative was obtained crystallising in orange-red needles melting at 251-252', identical with disccxobenxenep~~Ios.oglzcci~o2 monomethyl ether prepared previously from quercetin tetramethyl ether.These decomposition products prove t h a t this compound is the normal luteolin trimetlhyl ether, and with this i t s crystalline appearance and melting point are in harmony. The luteolin formed by the decomposition of this ether by means of hydriodic acid was compared with t h a t prepared from weld itself, The latter, purified as above stated by means of its hydrobromide to1320 PERKIN AND HORSFALL: LUTEOLIN. PART 111. remove apigenin, was now converted into the sulphate and this decomposed, as an extra precaution. The product crystallised in needles ; it melted a t 327-329', and its acetyl compound a t 222-225'. Luteolin, prepared by a 3 hours digestion of the trimethyl ether, crystallised from dilute alcohol in glistening leaflets melting at 314-316O; this was again treated with hydriodic acid for 2 hours, and was then obtained as needles.I t s acetyl compound melted at 222-225O, and the colouring matter regenerated from this at 323-326O. The final product separated as a mixture of needles and leaflets, and luteolin thus seems to crystallise in two forms. Luteolin from weld, after the removal of apigenin, is therefore most probably a single substance, for these results show its practical identity with the luteolin prepared from the trimethyl ether. Vongerichten (Ber., 1900, 33, 2334) has given the melting point of luteolin prepared from its monomethyl ether as 326-32S0, and in other papers, including that by one of us, it has been stated t o lie above 320O. As it appeared evident that weld does not contain methyl- luteolin, the formation of this compound as its trimethyl ether could only be due to the entrance of a methyl into the ring during methyla- tion.An attempt to prepare this compound by digesting luteolin trimethyl ether (1 gram) dissolved in a solution of potassium hydroxide (1 gram) in methyl alcohol with excess of methyl iodide for 2 days was unsuccessful, no change of this nature having occurred. Possibly the entrance of the methyl into the ring occurs simultaneously with the methylation of a hydroxyl group probably adjacent, and cannot be effected later, a t least in the above manner. It is interesting to note that the methylluteolin compound can be obtained from luteolin pre- pared from the Genista tinctoria (Zoc. cit.), and is also described by Von- gerichten as obtainable from the luteolin monomethyl ether contained in parsley (Zoc.cit.). LuteoZin Di.nm%yZ Ethel.. It was suggested by one of us that scoparin* (Trans., 1900,77,423) is a derivative of a luteolin monomethyl ether, possibly its stable glucoside. I n the hope of preparing this ether, which should have the methoxy-group in the 3' position, the partial methylation of luteolin was studied. * I n the preliminary notice on ecoparin (Proc., 1899, 15, 123), the investiga- tions of Goldschmidt and Hemmelmayr (MonatYh., 1893, 14, 202 ; 1894, 15, 316) have been overlooked. The recognition of the presence of a methoxy-group in scoparin, and its decomposition into phloroglucinol and acetovanillone, considered to be new a t the time, thus merely corroborate their work ; although this will be more fully explained in an investigation of scoparin which I hope shortly to com- municate, I take this opportunity of expressing regret t o these chemists that the oversight has occurred, -A, G .P.PERKIN AND HORSFALL: LUTEOLIN. PART 111. 1321 Five grams of luteolin dissoived in a solution of 3 grams of pot- assium hydroxide in methyl alcohol were treated with 12 grams of methyl iodide and digested a t the boiling point for 2 days. A deposit separated on cooling, and this was collected, washed with water con- taining a little sulphurous acid, then with alcohol, and repeatedly recrystallised from the latter solvent until its me ting point was constant. 0*1065 gave 0.1656 AgI. CH, = 9.92. C,,H,O,(O*CH,), requires CH, = 9.55 per cent.This ether formed a glistening mass of almost colourless needles, soluble in aqueous alkalis with a pale yellow coloration, and melted at 224-225O. The yield was small, amounting only t o about 8 per cent of the luteolin employed, and but little loss was experienced during its isolation owing to its sparing solubility in alcohol. It did not dye mordanted calico. To determine the position of the methoxy- groups in this substance, i t was decomposed with alcoholic potash a t 160". From the products G f thereaction, an acid was isolated in the form of colourless needles melting a t 250°, identical with isovanillic acid. The phenol simultaneously produced was not examined, as the fact that methylation can be effected by the method just described indicated that the hydroxyl group occupies the para- and not the ortho- position relatively t o the carbonyl group.It is interesting to note that Vongerichten's methyl ether of luteolin from parsley (Zoc. cit.) has its methoxy-group in the same position (4') as that occupied by one of those in the above compound. The mother liquors obtained in the purification of the dimethyl ether contained a mixture of substances, from which we are not yet satisfied that a pure product has been isolated. By fractional crys- tallisation from alcohol, an impure monomethyl ether was separated (found C = 64.16 ; H = 4031. CI6Hl2O6 requires C = 64-00 ; H = 4.00 per cent.), and this on decomposition gave isovccnillic acid. As an ether yielding in this way not isovanillic but vanillic acid mas the one desired, the above compound was not closely studied, but fur- ther experiment will now be made, as this should prove to be identical with Vongerichten's natural methylluteolin.The residue from the above methyl ethers gave shades, notably as regards the iron mor- dant, resembling in character although somewhat stronger than those given by scoparin. The subject will be further studied when a larger quantity of luteolin has been prepared.1322 PERHIN AND HORSFALL: I~UTEOLIN. PART III. Decomposition Product of Luteolin.. When fused with alkali to 170-200°, luteolin yields protocatechuic acid and phloroglucinol. If the tetrahydroxyflavone constitution assigned to it by one of us be correct, an acetophenone derivative, if i t possesses sufficient stability, should be formed at a lower tempern- ture under the conditions of the reaction.I n this manner, for instance, chrysin (dihydroxyflavone) and apigenin (trihydroxyflavone) give respectively acetophenone and p-hydroxyacetopheaone. Three grams of luteolin dissolved in 100 C.C. of a 50 per cent. solution of potassium hydroxide were digested at the boiling point for about half a n hour, or until a sample of the solution when neutralised with acid deposited only a trace of unaltered colouring matter, The yellow liquid was now acidified, extracted with ether, the extract evaporated, the residue dissolved in water, treated with excess of sodium hydrogen carbonate, and again extracted with ether. On evaporation, a n oily residue remained which crystallised on standing, and this was re- peatedly extracted with boiling benzene.From this solution, the bulk of the benzene was removed by distillation, and the crystals which separated from the residual liquid on cooling were collected and recrystallised from benzene with the aid of aliimal charcoal. 0,0647 gave 0.1506 GO, and 0,0327 H20. C = 63.47 ; H= 5.61. 0.1103 ,, 0.2555 CO, ,, 0.0545 H20. C = 63.17 ; H = 5.49. C,H,O, requires C = 63.16 ; H = 5.26 per cent. The product was deposited from benzene in needles containing benzene of crystallisation ; this evaporated at the ordinary temperit- ture and the compound then melted at 114-116'. With aqueous ferric chloride it gave a deep green liquid, and was decomposed by fused alkali at 200' with formation of protocatechuic acid, It was thus identical with the acetylcatechol, C,H,(OH),*CO*C H,, prepared synthetically by Dzerzgowski (J. Russ.Phys. Chem. Xoc., 25, 157). The residue insoluble in the benzene proved to be phloroglucinol, and these produ:ts con- firm the tetrahydroxyflavone constitution, 0 OH previously assigned t o luteolin by one of us. It is interesting to notice that whereas apigenin (Trans., 1897, 71, S17) has been shown to be hydroxychrysin, the above results indicate that luteolin is hydroxyapigenin.PERKIN AND HORSFALL: LUTEOLIN. PART III. 1323 Salts of Luteolin. It was found (Trans., 1899, '75, 433) that as a rule phenolic colour- ing matters containing two hydroxyls in the ortho-position relatively to one another decompose the alkali acetates, forming mono-substitu- ted salts.The prodicts then obtained from luteolin in this manner, being gelatinous, were not fully examined. Experiments now show that if a saturated alcoholic solution of luteolin is treated with potass- ium acetate, and then, while boiling, with a few drops of water, a crystalline salt separates on cooling. This was collected, washed with water, and dried at 160°. 0.4990 gave 0,1340 K,SO,. K = 12-03. 0.5053 ,, 0.1350 K,SO,. K = 11.97. 0.6559 decomposed with acid gave 0.5800 Cl,HlOO,. Cl,Hl,O, = 88.42. Monopotassium ZuteoZin forms fine yellow needles, and is decomposed by boiling water with separation of luteolin. It closely resembles the corresponding quercetin salt. The sodium compound is obtained by employing a dilute alcoholic solution of sodium acetate in place of the potassium salt.If crystals do not separate on cooling, water is added drop by drop, and the mixture boiled after each addition. The product is washed first with alcohol, then with water, and finally with alcohol. U15H,0,K requires K = 12-03 ; Cl,HloO, = 88.27 per cent. Analyses were made with distinct preparations. 0.3696 gave 0.0424 Na,SO,. Na = 3.71. 0.4968 ,, 0.0584 Na,SO,. Na = 3-80. C30Hl,01,Na requires Na = 3.87 per cent. The sodium salt of luteolin is thus analogous to the potassium salts of rhamnetin and rhamnazin (ZOC. cit.) as it is a mono-sodium derivative of a double molecule of the colouring matter. Summary of Results. On methylation, luteolin from weld yields, not only the normal trimethyl ether, but 8 second substance, which is regarded as methyl- luteolin trimethyl ether.This appears t o be produced by the entrance of a methyl into the ring of the phloroglucinol nucleus during the methylation process, rather than to result from the presence of methyl- luteolin (as glucoside) in weld itself, and i t is pointed out that luteolin from the Geaista tinctoriu (Zoc. cit.) and luteolin monomethyl ether from parsley (Vongerichten, Zoc. cit.), also yield this compound. By the ethylation of luteolin, Herzig (Zoc. cit.) has found that, in1324 HEWITT AND PERKINS: CONTRIBUTIONS TO THE addition t o the expected triethyl ether, a tetraethyl ether is formed t o some extent, so that, in these respects, this colouring matter be- haves analogously to resacetophenone (Gregor, Monatsh., 1894, 15, 437) and P-resorcylic acid (Trans., 1895, 67, 995). Curiously enough also genistein (this vol., p. 1310) forms two similarly constituted di- methyl ethers. Other members of the flavone group do not appear t o possess this property, for, as a general rule, the hydroxyl adjacent to the carbonyl group is not etherified in the ordinary manner of working, although Friedlander (Bey., 1897, 30, 2154) speaks of a chrysin dimethyl ether received from Piccard for purposes of comparison. Although there is little doubt that methylluteolin tri- methyl ether has the constitution assigned to it, it is proposed t o further investigate this substance in the hope of isolating methylphloro- glucinol from among its decomposition products. Much luteolin will be necessary for this purpose, and as this is difficult t o prepare, the publication of the results may be delayed for some time. The decom- position of luteolin into acetylcatechol and phloroglucinol practically establishes the tetrahydroxyflavone constitution previously assigned t o it (Zoc. cit.). In addition to luteolin, weld contains a trace of apigenin, and to this is no doubt due the slightly lower melting point previously assigned to acetylluteolin. CLOTHWORKERS’ RESEARCH LABORATORY, DYEING DEPARTMENT, YORKSHIRE COLLEGE.

ISSN:0368-1645    

DOI:10.1039/CT9007701314

出版商:RSC    

年代:1900

数据来源: RSC

摘要:

1324 HEWITT AND PERKINS: CONTRIBUTIONS TO THE CXXVI~.-Contributions to the Knowledge o f Fluorescent Compounds. P a r t I. The Nitro-derivatives o f Fluorescein. By JOHN THEODORE HEWITT and BRYAN W. PERKINS. IT is a remarkable fact that whereas the tetrabromo- and tetraiodo- derivatives of fluorescein show marked fluorescence in alkaline solutions, the corresponding nitro-compound exhibits no trace of this property. This fact has already been commented on by Richard Meyer (Zeit. physihl. Chem., lS97,24,468) and by one of the authors of the present communication (Proc., 1900, 16, 3 ; Zeit. physikal. Chem., 1900, 34, 1). Meyer, noticing that tetraiodofluorescein fluoresces less than tetrabromofluorescein, and this, in turn, less than fluorescein itself, would have been inclined to attribute the decrease in the fluorescence t o anKNOWLEDGE OF FLUORESCENT COMPOUNDS.PART I. 1325 increase in the mass of the substitueut groups, were it not that an a1 kaline solution of tetranitrofluorescein shows no trace of fluorescence whatever, although NO, = 46, whilst Br = 80 and I = 127. The view put forward by one of the present authors, that in the greater number of cases the fluorescence of organic compounds is caused by a doubly symmetrical tautomerism, furnishes a satisfactory explana- tion of the fluorescence of fluorescein, eosin, and tetraiodofluorescein where the only tautomerism possible is indicated in the following scheme : 0 C6H4- C0,H 0 0 whereas, for a nitro-derivative in which a nitro-group stands in the ortho-position relatively to a hydroxyl-group, it is not only possible, but indeed probable, that the nitrophenol group itself reacts tautometric- ally, producing a salt in which the metal is attached to the nitroxyl, and not t o the hydroxyl grouping.The sodium salt of tetranitro- fluorescein should then possess one of following constitutions : N0,Na N0,Na I I 0 II NO,O NO, o:/\/\A:o or NaNO,:I I I I:No,N~ 0 : / \ A / \ * o I I I* NO"/\/"NO2 \A/\/ Y->0 c6H, co >o C- C6H,- CO I I n this case, the configuration would be stable enough to preclude tautomerism, due t o the opening of the lactone ring, the oxygen of the hydroxyl groups having been previously transformed into the quinonoid form and sodium ions, thus losing their chance of migrating to the carboxyl group of the lactone ring.If this view were correct, an exactly similar argument should apply to dinitrofluorescein, but although the so-called hydrate of dinitro- fluorescein, which gives blue, non-fluorescent, alkaline solutions, has been prepared and analysed by von Baeyer (Annulen, 1876, 183, 32), the anhydrous substance of the formula C20H,o(N0,),05 does not appear to have been analysed. In purifying dinitrofluorescein, von Baeyer acetylated the crude product, recrystallised the diacetyl deriva- tive from alcohol or ethyl acetate, a.nd hydrolysed this by boiling with a solution of potassium or sodium hydroxide. On precipitation of the VOL. LXXVII. 4 x1326 HEWITT AND PERKINS: CONTBIBUTIONS TO THE resulting blue solution with an acid, a yellow substance was obtained, which, even after recrystallisation, again dissolved in alkalis with a blue colour, von Baeyer’s numbers for the compound agreeing with those required for the formula C,,H,,(NO,),O,. These results we can confirm, but by carrying out the hydrolysis of the diacetyl derivative with sulphuric acid instead of with an alkali, we have succeeded in obtaining the anhydrous dinitrofluorescein ; we have also introduced various modifications in methods of purification which considerably simplify the process.Although the anhydrous dinitro-derivative of fluorescein has been obtained and dissolves in cold alkali with the production of an orange- brown solution which evidently contains a salt of a substance of the formula C2,H10(N0,),0,, the nitro-groups act in the way which might be expected from the generally accepted views as to the constitution of salts of nitrophenols, and preclude the double tautomerism required for fluorescence which would otherwise result from the opening of the lactone ring.The fact that a solution, even if unstable, of a sodium salt of dinitrofluorescein has been obtained, is of considerable import- ance, since we have thus been able to examine a derivative of fluorescein which, although still possessing the pyrone ring intact, nevertheless shows no fluorescence in alkaline solutions. The real significance of this result will be observed when it is stated that not only are the usual salts of dinitrofluorescein derived from a hydrate, but that in the case of tetranitrofluorescein it has not, been possible t o isolate any substance other than a hydrate having the formula C20Hlo(N02)406.Any arguments which might be drawn from the non-fluorescence of the salts of the so-called tetranitrofluorescein are hence invalid. Preparation of Dinit~oJuorescein Hydrate.-In the nitration of fluorescein, von Baeyer’s directions with regard to temperature nesd careful attention. By following his instructions in adding 10 grams of fuming nitric acid t o 5 grams of fluorescein dissolved in 100 grams of concentrated sulphuric acid cooled to Oo, and pouring into water irnme- diately after the last addition of nitric acid has been effected, a bright yellow precipitate separates containing very little unaltered fluorescein, much of the dinitro-compound, and always some of the tetranitro- derivative.On the other hand, if the solution is allowed to stand overnight, tetranitrofluorescein is practically the only product, as it also is if the temperature is allowed to rise unduly. A very convenient method of separating the tetranitro- and dinitro-derivatives from one another is either to digest the mixture with a solution of sodium acetate, or to dissolve the whole precipitate obtzLined by pouring into water in hot, dilute sodium hydroxide, and then t o precipitate the dinitro-compound with acetic acid, the solution being allowed to coolKNOWLEDGE OF FLUORESCENT COMPOUNDS. PART I. 1327 before filtering, as the dinitrofluorescein hydrate is fairly soluble in hot water. The colour exhibited by an alkaline solution of the residue shows that it is an almost pure dinitro-compound ; for most purposes, i t is merely necessary to recrystallise the substance from hot alcohol, whereby small, orange, rhomboidal plates are obtained, which dissolve in cold alkali with a beautiful blue colour.The solution, however, occasionally shows a slight green fluorescence, due to the presence of unattacked fluorescein. If this is the case, i t is best to acetylate the product with acetic anhydride, and to recrystallise the acetyl derivative from glacial acetic acid until a sample gives an alkaline solution from which all fluorescence is absent. We confirmed the composition of the dinitrofluorescein hydrate so obtained by analysis 0,1393 gave 0.2799 CO, and 0.0335 H,O. C = 54.80 ; H = 2.67. 0,2155 ,, 12.1 C.C. moist nitrogen at 15' and 768 mm.N = 6.65. C,,H,,O,,N, requires C = 54.52 ; H = 2-75 ; N = 6.38 per cent. DiacetyZdinitroJEuorescei~,-O~ acetylating dinitrofluorescein hydrate, water is split off, and the diacetyl derivative of dinitrofluorescein pro- duced. This acetyl derivative also results on the acetylation of the crude product formed by adding nitric acid t o the sulphuric acid solu- tion of dinitrofluorescein, as von Baeyer has previously shown, whilst naturally i t may also be obtained, in better yield and of greater purity, by the action of acetic anhydride on the residue left after the crude nitration product is extracted with a dilute sodium acotate solution. It crystallises in colourless rosettes of needles from glacial acetic acid. On analysis : 0.1729 gave 0.3632 CO, and 0.0650 H,O.C = 57-28 ; H = 2.87. C,,H,,O,,N, requires C = 56.91 ; H = 2.76 per cent. When diacetyldinitrofluorescein is boiled continuously for 10 hours with a mixture of ethyl alcohol and water to which ethyl acetate is added to increase its solubility, a yellow solution is obtained from which, on evaporation of the ethyl acetate and cooling of the mother liquors, small, yellow crystals separate out which partially dissolve in hot sodium carbonate or cold sodium hydroxide (a residue of un- attacked diacetyl derivative being left) with an orange colour. On boiling with caustic soda, a blue colour is produced, as might be expected. The substance might be dinitrofluorescein from the colour of its soldtions, although this is impossible, since the continued boiling with ethyl alcohol and water would convert any such compound into the hydrate, which dissolves with a blue shade in cold sodium hydroxide.Since the diacetyldinitrofluorescein is insoluble in soda, there seems only one possibility left, namely, that water has been added on to the substance, and a hydrate of the constitution 4 x 21328 HEWITT AND PERKINS : CONTRIBUTIONS TO THE produced. The orange colour of the alkaline solution is precisely what might be expected from a nitrophenolic compound of this type. Tetrasodium Salt of DinitroJEuorescein Hydrate.-When a solution of an excess of sodium ethoxide in absolute alcohol is added t o a hot saturated alcoholic solution of dinitrofluorescein, an orange colour is observed changing to blue on the addition of a few drops of water.On stirring the solution, a crystalline, purple paste rapidly separates. This, when collected and washed with alcohol, was found t o contain 4 atoms of sodium per molecule. 0.1993 (dried a t 115') gave 0.1051 Na2S04. 0.2217 (dried a t 105') ,, 0.0923 NaC1. Na=17.30. C2,H80,,N,Na, requires Na = 17.42 per cent. Anhydrous DinitroJEuorescein, C,oH,,(N02),0,.-This substance may be obtained by heating the diacetyl derivative with five times its weight of 80 per cent. sulphuric acid for an hour on the water-bath. At first a clear brown solution was obtained, from which on further heating a canary precipitate separated, the remainder of the substance being thrown out by water. The dinitrofluorescein thus obtained was ground up t o a fine paste with water, well washed, and finally dried at 110'.Na= 17.04. 0.1347 gave 0,2832 CO, and 0.0325 H,O. C,,H,,O,N, requires C = 56.80 ; H = 2.39 per cent. The substance is sparingly soluble in strong alcohol, in which it dis- solves with a reddish-yellow colour showing no fluorescence ; the colour becomes somewhat green in shade on addition of a drop of hydrochloric acid. On long continued boiling with methylated spirit, i t dissolves with a red colour and shows no fluorescence, addition of water precipi- tating the hydrate. It is somewhat soluble in acetic acid, and fairly so in ethyl acetate, from which it separates in small, radiate aggregates of prisms. It dissolves in cold, dilute sodium hydroxide or in sodium carbonate solution with an orange-brown colour ; the solution exhibits no fluorescence.On warming a caustic soda solution, the colour soon changes to a deep blue, a salt of the hydrate being produced, but the orange or red solution in sodium carbonate does not become blue on boiling. The transformations experienced by dinitrofluorescein and its deriva- tives may be expressed by the following table : C = 57.33 ; H = 2.68.KNOWLEDGE OF FLUORESCENT COMPOUNDS. PART I. 1329 (CH,*CO),O. Dinitrofluorescein. &. Ditwetyldinitrofluorescein. Dinitroflnorescein G Diace tyldinitrofluorescein hydrate. NaOH. hydrate. In this scheme, the dotted lines represent changes which have not been confirmed by analyses of the products, diacetyldinitrofluorescein hydrate not having been isolated in a sufficiently pure condition for the purpose.Dibenxoyldinitro~uorescein, C,,H,(NO,),(CO*C,H,),O,.--This sub- stance was prepared by boiling 3 grams of dinitrofluorescein with 10 grams of benzoyl chloride in a reflux apparatus until the evolution of hydrogen chloride ceased. The product was then poured into alcohol, and stirred until the pasty substance 6rst precipitated became a brown, crystalline powder. This was collected, washed with alcohol, dried, and dissolved in boiling ethyl acetate. The solution was decolorised as far as possible with animal charcoal, filtered, and absolute alcohol added until the liquid began to show turbidity. On standing over- nigh t, a glistening, colourless, crystalline powder had separated, which, under the microscope, proved to consist of rhomboidal plates, the smaller angles of which were about 75".0.1626 gave 6.5 C.C. moist nitrogen a t 18' and 767 mm. N = 4-63. C,,H,,O,,N, requires N = 4-57 per cent. The substance dissolves fairly easily in acetone, ethyl acetate, or pyridine; i t is only taken up sparingly by benzene and ethyl alcohol. Its behaviour towards caustic soda solution corresponds with that of the diacetyl derivative. TetrccnitroJuorescein.--In preparing this compound von Baeyer acted on fluorescein with a considerable excess of fuming nitric acid (Annulen, 1876, 183, 33). We have found that by using corresponding quantities for dinitrofluorescein, but allowing the temperature to rise, or, preferably, the mixture to stand overnight, a very good yield of the tetranitro-derivative is obtained. This is isolated by pouring into water, when a pinkish paste separates, this is filtered, washed, and dis-1330 HEWITT AND PERKINS: CONTRIBUTIONS TO THE solved in a hot solution of sodium acetate. The solution is of n beautiful red colour, and, on cooling, deposits crystals of a sodium salt which, on recrystallisation, separates in small, brilliant red tetrahedra strongly resembling potassium dichroma,te in appearance.On precipitating the hot solution of the above sodium salt with a mineral acid, a pinkish- white precipitate is obtained, which, after drying, has the composition of a hydrate of tetranitrofluorescein. 0.1650 gave 0.2738 CO, and 0.0336 H,O. 0.1930 C = 45.26 ; H = 2.25. ,, 18.6 C.C. moist nitrogen at 24" and 768 mm. N = 10.81. 0.1948 ,, 18.0 C.C. ,, 9 , 24' ,, 754 mm.N= 10.49. C2,Hlo0,,N, requires C = 45.28 ; H = 1.90 ; N = 10.57 per cent, C2,H,O1,N, ,, C = 46.87 ; H = 1.56 ; N = 10.93 ,, Von Baeyer does not mention the existence OF a hydrate, but certainly our hydrate shows exactly the colour changes in alcoholic solution which he describes, namely, a yellowish-red colour with a yellowish- green fluorescence, the colour becoming reddish-violet on the addition of a drop of concentrated hydrochloric acid. Noteworthy is the fact that in alkaline solution no fluorescence is observed, which agrees well with the hypothesis of the conversion of the nitrophenol group into the quinone-isonitro-group on addition of alkali, I \ * NaN0,:C The analytical numbers obtained by von Baeyer agreed with those required for the formula C20H8(N02)405, and not with those for C2,H1,(N0,),06 ; his product was, however, recrystallised from glacial acetic acid. It seemed very probable, therefore, that the compound C,,H1,(N02),0, had become dehydrated by continued boiling with glacial acetic acid, especially since we had found that dinitrofluorescein hydrate, under similar conditions, yields a product soluble in alkali with an orange colour.We repeated the recrystallisation from acetic acid, and on analysing the recrystallised product were astonished to find that we were still dealing with the hydrate; a repetition of the experiment gave the same result, although the tetranitrofluorescein hydrate was boiled with 50 parts of glacial acetic acid for at least 10 hours. The analyses refer to the two different recrystallised prepara- tions.0.1855 gave 0.3096 GO, and 0.0480 H20. C=45*52; H=2.87. 0.1378 ,, 0.2280 CO, ,, 0.0306 H,O. C = 45.12 ; H = 2.47. The sodium salt above mentioned must be looked upon as a derivative of this compound, C20H,0(N02),06.KNOWLEDGE OF FLUORESCENT COMPOUNDS. PART I. 1331 0.4474 sir-dried salt lost 0-0870 H,O a t 110'. 0.3181 anhydrous salt gave 0.0900 Na,SO,. H,O = 19.44. C2,H,01,N,Na2,8H20 requires H,O = 20.06 per cent. C2,H,0,,N,Na, requires Na = 8.04 per cent. C,,H,O,,N,Na, ,, Na = 8.45 ,, Na = 8.12. A barium sah was obtained by boiling tetranitrofluorescein hydrate with barium carbonate and water so long as carbon dioxide was evolved, The filtered solution deposited small, red crystals on cooling ; these contained 4 mols. of water of crystallisation.0.3263 gave0.0308 H,O and 0.0979 BaSO,.* H20 = 9.45 ; Ba = 17.59. C20H801,N4Ba,4H20 requires H20 = 9.77 ; Ba = 18-62 per cent. Acetyl Derivcctive.-Von Bseyer mentions the preparation of an acetyl derivative, but gives no analytical data. We have also had such a compound in our hands, but also give no analyses, since every attempt a t a combustion ended with an explosion, even when thesub- stance was mixed with copper oxide in a bayonet tube. It is hoped t h a t analytical data will eventually be obtained, as it would be of interest to see if closure of the pyrone ring takes place during acetyl- ation. Constitution of the Nitro-derivatives of F2uorescein.-It will be seen from the experimental details communicated in this paper that the entry of nitro-groups into the fluorescein molecule in the ortho-posi- tions relatively t o the hydroxyl groups destroys the fluorescence, dinitrofluorescein giving an orange, non-fluorescent solution with caustic soda, although this solution readily turns blue on standing or heating, the elements of water being added on.This result is of con- siderable importance, since any arguments deduced from the non- fluorescent character of salts of tetranitrofluorescein are invalidated by the fact that this compound has only been obtained in the form of a hydrate.? Although there is no probability of dinitrofluorescein being other than a n o-nitrophenol derivative, it nevertheless seemed advisable to determine the orientation of the nitro-groups if this were possible. Dinitrofluorescein might equally well have eibher of the two formulae * We were unable t o obtain more satisfactory numbers for the percentage of barium, on account of the explosive nature of the salt.t The term hydrate has been used throughout this paper for the derivatives ob- tained by the addition of water to the fluorescein compounds. These substances, which really result by the opening of the pyrone-ring, are analogues of phenolphthalein and it would be more systematic to give analogous names to them, thus dinitro- fluorescein hydrate should be termed dinitroresorcinol-phthalein, &c.1332 HEWITT AKD PERKINS: CONTRIBUTIONS TO THE NO, 0 NO, 0 HO/'\/\/\OH or I I I I HO/\/\/\OH I I I I \/\/\/ C-- I >o 5:,->0 C,H,* CO C,H,*UO although the latter is, perhaps, slightly more probable, as it avoids so much crowding of substituent groups in the ortho-position.We endeavoured t o settle the point by fusion with alkali, a reaction very incompletely studied by von Baeyer (Zoc. cz't., 32). One of the products should be a nitroresorcinol, of which two have been de- scribed, the 1 : 3 : 4-derivative melting a t 115' and the 1 : 3 : 2- derivative a t 85' (Weselsky, Annalen, 1872, 164, 1 ; Monatsh., 1880, 1, 8 8 7 ; Flitz, Ber., 1875, 8, 631). Five grams of dinitrofluorescein hydrate were dissolved in 20 grams of 50 per cent. caustic potash solution and heated in a nickel basin until the blue colour had given place to a yellowish-brown shade. During the fusion, a certain amount of ammonia was evolved. The product was dissolved in water and acidified with hydrochloric acid, upon which a strong smell of hydrocyanic acid was noticeable.The liquid was filtered, the solid residue boiled with water, allowed to cool, and filtered, the operation being repeated several times. Nitro- resorcinol, if produced during the fusion, should be found in the aqueous extract, which was in consequence repeatedly shaken with benzene. On distillation of the benzene extract, a small residue was obtained which, after two recrystallisations from water, with the addition of animal chrircoal, gave a suficient quantity of minute yellow crystals for the determination of a melting point. This was found to be 114' (uncorr.). One point further has to be considered, namely, the position in the molecule where water is added on in the production of the so-called hydrates.I n 18'76, von Baeyer assumed that, in the production of fluorescein, oxide or ether formation took place between hydroxyl groups of the two resorcinol molecules, which condense with one molecule of phthalic anhydride. On the conversion of a fluorescein compound into a hydrate, this oxygen atom was supposed to take up a molecule of water, the change being represented by the equation On the substitution of the lactone for the diketonic formula for fluorescein, the idea seems to have arisen that water was added to theKNOWLEDGE OF FLUORESCENT COMPOUNDS. PART I. 1333 lactone group. For example, in Beilstein's Hccndbzcch (2 te Aufl. Bd. 11. , 1296) dinitrofluorescein is formulated as O[C,H2(N0,)OH],C(OH)*CGH4*C02H.Such an expression seems t o us to be untenable; in its place we would substitute a formula in which the addition of water resulted in the splitting of the pyrone ring in the following manner : 0 The grounds on which this view is based are as follows. 1. Fluorescein itself is very stable towards alkali, the tetrabromo- derivative takes up water more easily than fluorescein, whilst with di- nitrofluorescein the hydrate is the stable form and with tetranitro- fluorescein the hydrate is the onlyform we have so far been able to isolate. Negative groups introduced into a benzene nucleus are known t o influenceother groups in the same nucleus and especially when the substituents are in ortho- or para-positions relatively to one another. That the negative groups should influence the extranucleal lactone ring, however, is, so far as we are awnre, without analogy. 2. Tbe pyrone ring of fluorescein is evidently weakened by the intro- duction of nitro-groups as shown by the fact that an acridine derivative results when dinitrofluorescein is treated with cold ammonia solution (Reverdin, Ber., 1897, 30, 333). 3. The blue colour of the solution of dinitrofluorescein hydrate in alkali is not dissimilar to the colour exhibited by the phthaleins; at any rate, it resembles this far more than the red or brown solutions produced when fluorescein or flnorone derivatives are dissolved in an alkali. This argument does not lose in weight by the fact that dinitro- fluorescein itself dissolves in cold alkali with a n orange shade. 4. The formationof a tetra-sodium salt from dinitrofluorescein hydrate affords fairly conclusive evidence in favour of this view ; had the lac- tone ring been opened a trisodium salt would be expected, as is shown on consideration of the two possible formule : 01334 FLUORESCENT COMPOUNDS. PART I. As a result of this work the conclusion may be drawn that the introduction of nitro-groups into the fluorescein molecule in the ortho- position relatively to the hydroxyl groups prevents fluorescence in alkaline solutions, owing to the usual phenol-lactone and quinonoid- carboxylic acid tautomerism of fluorescein being inhibited by a secondary tautomerism between the nitro- and phenolic hydroxyl groups. A t the same time, the pyrone ring is so much weakened that water is readily added on with production of a true phthalein. EAST LONDON TECHNICAL COLLEGE.

ISSN:0368-1645    

DOI:10.1039/CT9007701324

出版商:RSC    

年代:1900

数据来源: RSC

摘要:

INDEX OF AUTHORS’ NAMES. TRANSACTIONS. 1900. ( M a r l c d T.); and also to Proceedings of the Session 1899-1900, Nos. 413 to 226, Nov., lt399-June, 1900 (marked P.). COMPILED BY MARGARET D. DOLTGAL. A. Adie, Richard Hcdibtct tot?, sul1)hotes of bismuth, P., 1899, 226. Adie, Richard Haliburton, and KeiidnZZ C‘olin Browning, interaction of sulph- uric acid and potassium ferro- cyanide, T., 150 ; P., 1899, 226. Adie, Kic?iccrd Haliburton, and TJmiccs Earlow Wood, a new method of csti- mating potnssiuni, T., 1076; F. , 1900,17. Allen, Richard IC‘illitcm, the niaximuiii pressure of naphthalene vapur, T., 400 ; P., 1899, 122. - the maximum pressure of caniplior vapoiir, T., 413 ; P., 1899, 135. Armstrong, Heary Edzoard, yhenyl- acetvlchloramiiie and its analogues. - U I T., i 0 4 7 ; P., 1900, 160.- azo- and hydrazone compounds differentiated by bromine, P., 1899,243. - note on BRcli’s hydrogen tetroside, P., 1900, 134. Armstrong, Reiwy Edward, and ll? Berry, meta-sulphonation of ariiliiie, Armstrong, Hcxry Ediuard, and P e m ~ C. C. Isherwood, broniiiiation of osyazo-compounds, P. , 1900, 158. Armstrong, Henry E d m w d , and E(=tlzuard 1V. Lewis, inhibiting effect of ethcri- fication on substitution in phenols, P., 1900, 157. Armstrong, Henry Edward, and Sidiwy Swivener Napper, benzcne-o-disulph- onic acid, P., 1900, 160. Aston, William George. See JoJm Theodore Re wit t. P., 1900, 159. VOL. LXXVII. Auden, ITarold AZlde?z, some new osa- zoxies and tetrazones, 1’. , 1899, 229. B. Baker, H. Brereton, vapour density of dried mercurous chloride, T., 646 ; P., 1900, 68 ; discussion, P., 68. Baker, Jiclian Levett, and Thomas Henry Pope, niaiinogalactan and Iaxuloman- nan ; two new polysaccharides, T. , 696 ; P., 1900, 72. Baker, T. J., heat of combination of copper with zinc, P., 1899, 195. Beddow, F,*edcrick. See Siegfried Ruhemann. Berry, It.‘. See Henry Ei2~cttt-d Arm- strong. Blzckman, W c i Itey Lioiael. See Keinictly Joseph Precite Orton. Bloxam, JViZZiam PoppZewell, hydrosul- pliides, sulpliidcs, and polysulphides of 1)otassium and sodium, T., i53 ; P., 1899, 146. Bone, l17illiam Ai‘tliw, and ChnrZcs H. G. Sprankling, researches on the alkyl-substituted succinic acids. 11. s-Dipropyl-, s-diisopropyl-, and aal- ~)rop~lisopropyl-succiilic acids, T. , 654 ; l’., 1900, 71. -- rezearches on the alkyl-substi- tuted succinic acids.Part 111. Dissoci- ation coiistants, T., 1298; P., 1900, 181. Bottomley, J. Prank, and WiZZiam Hewy Perkin, jzm. , coildensation of formaldchyde with ethyl malonate, and synthesis of pentamethylene-l:2:4- tricwhosylic acid, T., 294 ; P. 1900,16. 4 Y1336 1NT)EX OF AUTHORS. Bowtell, N. A’., a n d William €Ie?wy Perkin, jun., actiou of alcoholic potash 011 ethyl hromoglutarate, P., 1899, 241. Browning, Ke?idnll Colin, hydroferro- cyanic a d , T., 1233 ; l’., 1900, 172. Browning, Kendall Colin. See also Richard Haliburton Adie. Bunsen, Robert FVillzelm, memorial lecture on (Roscoe), T., 513 ; P., 1900, 84. C. Carter, T., and William Trevor Law- rence, the hydroxyphenoxy- and phenylenediosy-acetic acids, T., 1222 ; P., 1900, 152.Caven, Robert Marti?&, reaction of mag- nesium, zinc, and iron with solutions of cupric sulphate, P., 1899, 232. Chapman, Edgar Marsh. See Arthw Lapworth. Chattaway, Frederick Daniel, and Ken- ncdy Joseph Previte Orton, substituted nitrogen chlorides and their relation to the substitution of halogen in anilides and anilines. 11. Trichloro- phenyl acyl nitrogen chlorides, T., 134 ; I?., 1899, 232. -- substituted nitrogen chlorides and bromides derived from o- and p-acetotoluidide, T., 789 ; P., 1900, 102. -- ortho-substituted nitrogen chlorides and bromides and theentrance of halogen into the ortho-position in the transformation of nitrogen chlor- ides, T., 7 9 7 ; P., 1900, 112; dis- cussion, P., 112. Chattaway, Frederick Daniel, Kei~nedy Joseph Previte Orton, and 1V.H. Hurtley, nitrogen chlorides derivable from m-chloroacteanilide and their transformation, T., 800 ; P., 1900,125. Collie, John Norntnn, dehydracetic acid, T., 971 ; P., 1900, 147. Collie, John Norman, and Bertram D. Steele, dimethyldiacetylacetone, tetra- methylpyrone, and orcinol derivatives from diacetylacetone, T., 961 ; P., 1900, 146. -- periodides of substituted os- onium derivatives, T., 1114; P., 1900, 164. Cormack, William, estimation of furfur- aldehyde, T., 990 ; P., 1900, 156. Cormack, WilZiam. See also James Walker. Crafts, James Mason, Friedel Memorial Lecture, T., 993. Crofts, James Murray. See Ro6ert &lby Morrell. Crossley, Admr IVillicrm, interaction ofmesityl oxide and ethyl sodiomethyl- malonate, P., 1900, 90. Crossley, Arfhzrr IViZlicrm, anti 11, niy RoiitZel Le Sueur, determination of the constitntion of fatty acids.Part 11. , T., 83 ; P., 1899, 225. D. Davis, tVL?Zia?n A l j k d , etlierification of derivatives of &naphthol, T., 33 : P., 1899, 210. Dawson, Haw?/ Jledf’ortk, and John YcCrae, the nature of metal-ammonia compounds in aqueous solution. Part I., T., 1239; P.: 1900, 172. Dawson, Harry Ardforth, and P. Williams, determination of transition ternperaturcs, P., 1899, 210. Dean, George, atomic weight of nitrogen, T., 117 ; P., 1899, 213. Divers, Edward, the colour of alkali nitrites, P., 1900, 40. - solubility of mixed potassium nitrite and nitrate, P., 1900, 40 ; discussion, P., 40. - products of the action of sulphur dioxide on ammonia, P., 1900, 1 0 4 ; discussion, P., 105.Divers, Rdzoard, and Tamemasa Haga, potassium nitritohydroximidosnlph- ates, and the non-existence of di- hydroxylamine derivatives, T., 432 ; P., 1900, 54. -- identification and constitntion of Fremy’s sulphazotised salts of potass- ium, T., 440 ; P., 1900, 55. -- the interaction between sul- phites and nitrites,T., 673; P.,1900,70. -- decomposition of hydroxy- amidosulphates by copper snlphate, T., 978 ; I’., 1900, 147. Divers, Eiiward, and Masataka Ogawa, ammonium amidosulphite, T., 327 ; P., 1900, 38. -- products of heating ammonium sulphites, thiosulphate and trithionnte, T., 335 ; P., 1900, 39. -- ammoninm imidosulphite, P., 1900, 113. Dobbie, James Johmtone. See FValfeY AToel Har tle y. Dootson, Frederick William, condensa- tion of methyl acetonedicarboxylate : constitution of orcinoltricarboxylic esters, T., 1196 ; P., 1900, 170, Dootson, Frederick TV’ilZinm.See also William James Sell. Drugman, Julien, and William Ramsay, specific gravities of the halogens at their boiling points, and of oxygen and nitrogen, T., 1228 ; P. , 1900, 172.INDEX OF AUTHORS. 1337 Dunstan, Wyndhaiil Rodaiid, and flrncst Goulding, action of all~alis on the nitro compounds of the paraffin series. Part 11. Reaction, ail11 con- stitution of nietliazonic acid niid the mode of formation of isowzolw, T., 1262 ; P., 1900, 174. Dunstan, J V ~ ~ ~ ~ J ~ C ( I ~ L Ihrc l m d , and Harold X. Read, contribotioiis to our kno~vledge of the aconite alkdoiils. Part XV. On jnpaconitine and the alkaloids of Japanese aconite, T., 45 ; P., 1899, 206 ; discussion, P., 207.E. Edmed, Frmk Qcorg’gs, note on the action of dilute nitric acid on oleic and elaidic acids, P., 1899, 190 ; discus- sion, P., 191. Elliott, WaZtcr JOJLIL, action of chloro- form and potassium hydroxide on o-aminobenzoic acid, T., 213 ; P., 1899, 243. Eynon, Lewis. See E c q h ~ l Meldola. F. Fenton, H&ili*y Joli n Horstinnn, degra- dation of glycollic aldehyde, T., 1294 ; P., 1900, 148. Fenton, Hcm-y J o h HorstmmL, and Hicmphwy OweiL Jones, the osic1:ition of organic acids in presence of fcrrous iron, T., 69 ; P., 1899, 223. -- oxalacetic acid, T., 7 i ; P., 1899, 224. Forster, Ilfcwti?b OiisZow, studies in the camphalie series. I. Xitrocamphane, T., 251 ; P., 1900, 13. Forster, Martiit Oi1slozL1, and Jcciiics Hart- Smith, separation of neobornylainine from bornylamine, T., 1152 ; P., 1900, 166.Fortey, Emily C. Francis, Fmiicis E., isomeric clibcnzyl ketone benzalanilines, and deoxy bcnz- oin benzalanilines. Part l I . , T., 1192 ; P., 1900, 169. Friedel, Chndcs, Memorial Lecture on (Crafts), ‘l’., 993. See Spliiey Young. G. Gardner, Jehu Addpian, note on the bromo-derivatives of camphopyric acid, P., 1900, 46. Gilbody, ,4 lcxaiitler lVillia??%, and Willircin Hcnry Perkin, jun., brazilin and haeniatoxylin, P., 1899, 241. Gilbody, Alcxaitder lvillinm, WiZZinm Hcwy Perkin, $n., and J. Yates, on brazilin, IV., l‘., 1900, 105. Goulding, Emcst. See TVy~~Jharn Eow- Zmid Dunstan. Goyder, Ir’corgc A . , sulvaiiite a new mineral, T., 1094; l’., 1900, 164. H. Haga, T~I~IZCIILCIS~. See Etltun~el Divers.Hall, Ha~oltl, See A.crlc?.ic S t n d c y Kipping. Harkness, TViZliatii, obituary notice of, T., 592. Hartley, TF’edtcr A’ocZ, two hydrated cobalt oxides, green- and bntf-coloured, P., 1899, 202. Hartley, 1Valtcr ,J-od, and Jmics Johii- stone Dobbie, absorption spectra of ammonia, methylamine, hydroxyl- amine, aldoxiine, and acetoxirne, T., 318 ; P., 1900, 14. -- spectrographic studies in tau- tomeiisni : the absorption curves of the ethyl esters of dibenzoylsuccinic acid, T., 498 ; P., 1900, 57. -- the curves of the molecular vibrations of benzn,dialdosime aiid benzn2/naldosiirie, T., 509 ; P., 1900, 58. -- ultra-violet absorption spectra of some closed chain carbon com- pounds. Part IT. Dimethylpyrazine, hexnmetliylene, and te trahydrohenz- enc, T., 846 ; P., 1900, 129.Hartley, llrdtrr NocZ, Jniizes Johnstonc Dobbie, and PI~otios G. Paliatseas, a study of the ahsorption spectra of o-oxycarbanil ant1 its alkyl derivatives i n relation to tautomerisrn, ‘l’,, 839 ; P., 1900, 130. Hart-Smith, Jctntcs. See X w t i i i Oiulozo Forster. Harvey, A@ed lVi?Ziain. See TYilliuttz Jackson Pope. Hewitt, John Thcodore, preparation of benzeneazo-o-nitrophenol, 1’. , 99 ; P . , 1899, 229. - relation between the constitution and fluorescence of some substances, Hewitt, John Thcotlore, and 7YilZiam Gcorgc Aston, bron: ination of benzene- azophenol, I. and II., T., 71?, 810 ; P., 1900, 89, 131. Hewitt, John Theodore, and Bryan 1V. Perkins, contributions to the know- ledge of fluorescent compounds. Part I. The nitro-derivatives of fluores- cein, T., 1324 ; I’., 1900, 178.P., 1900, 3. 4 ~ 21338 INDEX OF AUTHORS. Hibbert, H. Hodges, Johiz Frederick, obituary notice of, T., 593, Hodgkinson, Tilliam Eiclt n rd Eoton, and Lconhwd Limpach, a method of separation of the various isomericles contained in ordinary commercial xyliti- ine, T., 65; l'., 1899, 202. Horefall, Lowis liubert. Sce llrtJvur Oeoyge Perkin. Howles, Fred H., Jocclyi P d t l Thorpe, William Udall, and in part 15. A . Neale, B-isoyropylglutaric acid and cis- and trans-me thy lisopropylglu tnric acids, T., 942; P., 1900, 115. Hurtley, 1V. H. See I"rc.rlcrick Drrii icl Chattaway. See J. P. Millington. I. Isherwood, Percy C. C. See Hc;t,y Edward Armstrong. J. Jackson, V c i ~ r y , forination of a- and B- acrose from glycollic aldehyde, T., 129 ; P., 1899, 238.Japp, Francis Robert, and Jmzcs Poir, constitution of amarine, of its supposed clialkyl- and diacyl-derivatives, and of isamarine, T., 608 ; P., 1899, 211, 227 ; 1900, 15. Jones, liumphrey Owen. See Hcwy John Horstmax Fenton. Jowett, Booper AZbcrt Dickinvou, pilo- carpine and the alkaloids of jnborandi leaves, T., 473; P., 1900, 4 9 ; di+ eussion, P., 50. - new glucoside from willow bark, T., 707 ; P., 1900, 89. - coiistitutioii of pilocarpine, T., 851 ; P., 1900, 123. K. Kinch, Edzcwd, amount of chloiine in rain water collected a t Cirenccster, T., 1271 ; P., 1900, 133. Kipping, Frcdcric Xtnnlcy, isomeric partially racemic salts contailling quinqiievaleiitnit~ogen. Partsl. -VI. Hydrindamine bromo- and clilnro- cnmphorsulphonates, nncl ci,:-~-c:ii~l- phaiiates, T., 8Vl ; P , 1900, 51.- note on the decninposition of seini- -carbazones, P., 1900, 63. Kipping, Fmderic Stanley, and Harold Hall, new syntheses of indene, T., 467 ; P., 1900, 54. Kipping, e ' c l r ) ic S t i i / i l i , L / ant1 H(iroltl Peters, iodonium coinpoiinds of the tylw Ilt' 11" K1l1 niid the co1ifig~r:~- tion of the iodine atom, P., 1900, 62. L. Lander, Gcorge DIVCC, alkylation by means of dry silver oxide and alkyl halides, T., 729; I?., 1900, 6, 90. Lapworth, AAJlw, tleiivatives of cyano. caml)hor and of liomocamphoric acid, T., 1053 ; P., 1900, 128. -- on the function of the characteristic nieta-orientating groups, P., 1900, 108. - coiiclensation of ethyl crotonate with ethyl oxalate, P., 1900, 132. Lapworth, Arthzcr, and Edgar i l h - s l i Chapman, action of fuming nitric acid on a-dibromocaniphor, T., 309 ; 1'., 1900, 4. -- camphonic, homocamphoronic, and caniphononic acids, T., 446 ; 1'. , 1900, 56. Lawrence, 1Villinm Trcror, the con- drnsation of ethyl a-bromoisobutyrate with ethyl malonates and ethyl eyano- acetates : a -methy 1-al-isobutylglutaric acid, I)., 1900, 154. - methylisoamylsuccinic acid, II., I?., 1900, 156. Lawrence, lViZ?&im Trcro~. See also lV. Carter. Lean, J:cmn, ethyl dibromobutane- tetrncnrboxylste and the synthesis of tetraliydro furfuran- 2 : 5 - d icarbosylic acid, T., 103; P., 1899, 197. Lees, I"rcr7crick H., and 1C'iZliam Hcwy Perkin, jm., action of aluminium chloride on camphoric anhydride, III., P., 1900, 18. Lees, Frederick H.See also Snnwccl Bnrnctt Schryver. Le Sueur, Hewy Roiadcl, products of the wtioii of fused potash on dihydroxy- stearic acid, P., 1900, 91. Le Sueur, Hens.?/ Eoliclel. See ArtA U Y Willicm Croasley. Lewis, Edward It.'. See Howy Eih-cn~d Arms trong. Lewkowitsch, Jdiits, the theory of s~ponification, P , 1899, 190 ; dis- ciissioii, P., 190. Limpach, Leo?Lhnrd. See 1ViZlimn iiwhard Enloi~ Hodgkinson. Lowry, Thomas Mri?tin, and John 37. West, the persulphuiic acids, T., 950 ; P., 1900, 126.Ih'lIEX OF AUTHORS. 1339 M. lcCrae, John, and T. S. Patterson, acetyl and phenacetyl deiivativei of diethyl &tartrate, T., 1096 ; P., 1900, 161. IcCrae, JohTt. See also ~ ( ~ I T I J Xed- forth Dawson. l a l l e t, Prederic Rich a i *ct; ~ a a h y 11 row sulphates of the form 2hT ,SO,, R',SO, : especially those of isometric cryst%llis- ation, T., 216; P., 1899, 22i.Marcet, William, obituary notice of, T., 594. larchlewski, [ P c ~ d ] Leon [ Thcodot*c], and C. A . Schnnck, notes 011 the chemistry of chlorophyll, T., 1030 ; P., 1900, 148. latthews, Fruncis Edworcl, liexachlor- ides of benzonitrile, beiizamide, and benzoic acid, T., 1273 ; P., 1900, 175. leldola, hphncl, and Lcicqis Eynon, aminoamidines of the naplithalene series, T., 1159 ; P., 1900, 166. leldola, Raphack, and .EZlcc61~ Wechsler, note on the eliniinatioii of a nitro- group during diazotisation, T., 1172 ; P., 1900, 167. Meldola. Eaphnel. and TViZlirtllL ,lrthuy Williams, Lnotesbn i~olyazo-compouads, P., 1899, 196. Ieyer, Victor, nieniorial lectnre 011 (Thorpe), T., 169; P., 1900, 33.Millington, J. P., and H. Hibbert, an isomeride of fiirfurine, P., 1900, 161. Mills, William Sloan, cliphenyl- and dialph 1-ethylenedianiines, and their nitro-Lrivatives, nitrates, and mer- curichlorides, T., 1020; P., 1900, 127. l o b , James. See F?*a?Lcis 8obel.t Japp. Morgan, Gilbert TJionans, action of form- aldehyd? on amine~ of the napthal- ene series. Part II., T., 814; P., 1900, 131. - contribution t o the clieniistrg of the aromatic inetadiamines, T., 1202; P., 1900: 170, - action of aromatic aldehydes on derivatives of 8-naphthylaniine, T., 1210; P., 1900, 171. l o r r e l l , f i b w t Selby, and Jantes 2Clicrrcq Crofts, action of hydrogen peroxide on carbohydrates i n the preesence of ferroas salts, II., T., 1219; P., 1900, 171.N. Napper, Sidney Scriveiier. See Henry Nettle, H. A. Edward Amstrong. See Fred H. Howles. Newth, Gcorgc S., note on partially inisciblr? aqiieous inorganicsolutions, T., 775 ; P., 1900, 87 ; discussion, P., 88. - liciuefactioi: of a gas by '' self-cool- ing " (a lecture experiinent), P., 1900, 87. Nilson, Lnrs F~"crZr.iX-, 1Ieiiiorial Lecture 011(Petter.json),T., l2i7; P., 1900,163. 0. Ogawa, i~~OX6/~lkU. See Erl.zon~d Divers. Ogston, Gmye Bcnry, obituary notice of, T., 594. Orton, Ke?incil!g Joscph Pmvitc, and Waltw Lionel Blackman, estimation of hypoioclites and iodates, and the reaction of iodine monochloride with alkalis, T., 830 ; P., 1900, 103; dis- cussion, P., 104. Orton, I<emwZy JOS,~IJL Pivvitc. See also I;;-cdcl*icX3 Drciiid Chattaway. 0' Sullivan, James, presence of invertase in sonie plants of tlie Graniinece, I., T., 691 ; P., 1900, 61.Oxland, I:oBci*t, obituary notice of, T.) 596. P, Paliatseas, Photios G. Hartle y. Patterson, T. S. Peachey, Sfccdey John. See Willici I I L J(tckson Pope. Perkin, A T t h u v Geoiyc, apiin a i d api- genln. Part 11. Note on vitexin, T., 416 ; P., 1900, 44. - yellow colonring princirles contained in various taiiniii matters. Part VII. A rctostnplbylos Urn zirsi, Htcnlntoxylon ~n,ii~ccicJLiccizu?12, BJL 11s J f c t o p i t ~ t , J1y17iCt6 Gale, Coriarin rizyrtifolia, and Bobinin Pscudncncin, T., 423 ; P., 1900, 45. See 1Valter Nod See Johic YcCrae. - luteolin, III,, P., 1899, 242. Perkin, AdJzi!r Georgc, and Louis HZL- bcyt Rorsfall, genistcin. Part II., T., 1310 ; P., 1900, 182.-- luteoliii. Part III., T., 1314 ; P., 1900, 181. Perkin, Williccm Heqzvy, refractive and 111 ignetic rotatory powers of some benz- enqid hytlrocarboiis : refractive poFers of niixtnres : improved spectrometer scale reader, T., 267 ; P., 1899, 237 ; discussion, P., 238. Perkin, TviEinsia settry, jun., and Jocclp~ Ficld Thorpe, experiments on the synthesis of camphoric acid. 111. The action of sodium and methyl iodide on ethyl dimethylbntanetricarb- oxylate, P., 1900, 152.1340 INDEX OF AU'I'HORS. Perkin, H%%hn Hewry, jtcn., Jocclp Field Thorpe, aiid C. Walker, a new series of pentamethylene derivatives, Perkin, William Reizry, j m . , and J. Yates, on hzematoyxlin, V., P., 1900, 107. Perkin, William Heitry, j i i n . Sce also J. Fraizk Bottomley, AT.E. Bowtell, Alczaizder William Gilbody, and Frederick I?. Lees, Perkins, Brgan W. See John T7wodorc He wit t . Peters, Hnrold. See Frcdcric Stndcy Kipping. Pettersson, Otto, Nilson Memorial Lec- ture, T., 1277; P., 1900, 163. Plimpton, Bichard !/?a@, obituary notice of, T., 595. Pope, l'ho~iac~s 11ei~ry. See Jidinit Lcvctt Baker. Pope, TVillinm Jkckson, and Avrcd William Harvey, racemisation occur- ring during the for:nation of benzylid- ene, benzoyl, and acetyl derivatives of d-ac-tetrahgclro-B-iiaphtiiylaniine, Pope, William Acckso~~, and Stav ley JOJL?Z Peachey, asyininetric optically active sulphur compounds : d-niethyl- ethylthetine platinichloricle, T., 1072 ; P., 1900, 12. -- asynimetiic optically active tin compomids : d-methylethyl-wpropyl tin iodide, P., 1900, 42.-- the racemisation of optically active tin compounds : cl-methylethyl- propyl tin d-broniocampliorsulp2ioi~atc, P., 1900, 116 ; discussion, P., 117. I . , P., 1900, 149. P., 1900, 74. R, Ramsay, William. See JtcliciL Drug- man. RB y, Prnfulln Chawh-n, interact iou of mercurous nitrite and ethyl iodide, P., 1899, 239. - mercurous iodide, P., 1899, 239. Read, Harold M. See Wyndham Row- land Dunstan. Reynolds, Henry Charles, obituary notice of, T., 596. Reynolds, Jcmes Emersoii, researches on silicon compounds. Part VI. On silicodiphenyldiimide and silicotri- phenylguanidine, T., 836 j P., 1900, 133. Roscoe, Sir Heiiry EnJield, Bunsen Nemorinl Lecture, T., 513 ; P., 1900, 84. Rose, Thomas Xirlie, note on Volhard's method for the assay of silver bullion, T., 232 ; P., 1900, 5.Ruhemann, Sicg fr ied, and Frederick Beddow, condensation of phenols with esters of the acetylene series. Part I. Action of phenols on ethyl phenylprop- iolatc, T., 984 ; P., 1900, 123. -- coildensation of phenols with esters of the acetylene series. Part 11. Action of phenols on ethyl phenylyrop- iolate and etliyl acetylenedicnrboxyl- ate, T., 1119 ; P., 1900, 165. Ruhemann, Siecj@icil, and Henry Ernest Stapleton, formation of heterocyclic compounds, T., 239 ; P., 1900, 11. -- condensation of ethyl acetyl- enedicnrboxylate with bases and 8-ket- oiiic esters, T., 804; P., 1900, 121. -- condensation of phenols with esters of the acetylene series. Part 111. Synthesis of benzo-y-pyrone, T., 1179 ; P., 1900, 168. Russell, Etlwam! JO~LIZ, notes 011 the estimation of gaseous compounds oE snlphnr, T., 352 ; P., 1900, 41.- influence of the nascent state on the *combination of dry carbon mon- oxide and oxygen, T., 361 ; P., 1900, 42. Russell, Edionrd Johic, and Norinan Smith, the conibinatioii of sulphur dioxide and oxygen, T.,, 340 ; P., 1900, 41. S. Schryver, ~ ( ( L P I L Z C C ~ Barwett, and Frederick H. Lees, researches on morphine. Part I., T., 1024; P., 1900, 143. Sohunck, C. A . See Leon Marchlewski. Scott, Alexandev, preparation of pure Iiydrobroinic acid, T., 648 ; P,, 1900, 69. - a new snlphide of arsenic, T., 651 ; P., 1900, 69. Sell, William James, a i d Fredeqe?'ick William Dootson, the chlorine deriv- atives of pyridine. Part IV. Coii- stitution of the tetrachloropyridines, T., 1 ; P., 1899, 205.-- chlorine derivatives of pyrid- ine. Part V. Constitution of citra- ziiiic acid : formation of 2: 6-dichloro- pyridine and 2: 6-diiodoisonicotinic acid, T., 233 ; P., 1900, 9 ; discussion, r., 11. -- chlorine derivatives of pyrid- ine. Part VI. Orientation of some chloroaminopyridines, T. , 771 ; P. , 1900, 111.INDEX OF AUTEORS. 1341 Silberrad, Oswald, contributions to t h chemistry of hydrotetrazines anc triazoles, T., 1185; P., 1900, 169. Slosson, E. E. Smedley, Ida, benzylanilinesulphoni~ acids, P., 1900, 160. Smiles, Saniuel, action of alkyl iodider on the mercuric iodide sulphides o the fatty series, T., 160; P., 1899. 240. -acontribution to the stereochemistry of sulphur : an optically active sulyh- ine base, T., 1174; P., 1900, 168. Smith, Norman.See Edwurd John Russell. Snape, Henry Lloyd, racemic and optic- ally active forms of amarine, T., 778; P., 1899, 228 ; 1900, 118. Sodeau, William Horace, decomposition of chlorates, with special reference to the evolution of chlorine and oxygen, T., 137; P., 1899, 157. - decomposition of chlorates. 11. Lead chlorate, T., 717; P., 1900, 88. Sprankling, Charles B. C. See William Arthur Bone. Stanford, Edwurd Charles Cortis, obitu- ary notice of, T., 597. Stapleton, Henry Ernest. See SielXfried Ruhemann. Steele, Bertram D. See John Norman Collie. Stieglitz, Juliw, and E. E. Slosson, note on nitrogen halogen compounds, Sworn, Sidney Augustus, obituary notice of, T., 598. Szarvasp, Emerique Charles, electrolytic preparation of induline dyes, T., 207; P., 1899, 194.- electrolysis of the nitrogen hydrides and of hydroxylamine, T., 603; P., 1900, 3. See Julius Stieglitz. P., 1900, 1. T. Taylor, Robert Llewellyvq action o f iodine on alkalis, T., 725; P., 1900, 70. Thorp, William, obituary notice of, T., 599. Thorpe, Jocelyn Field, constitution of ethyl sodiocyanacetate and of ethyl sodiomethylcyaiiacetate, T. 923 ; P. , 1900, 113. Thorpe, Jocelyn Field, and William J. Young, cis- and trans-aa,BB-tetra- methylglutaric acids, T. , 936; P., 1900, 114. Thorpe, Jocelyn Field. See also Pred H . Howles, and William Eenry Perkin, jun. Thorpe, Th,ornas Edward, Victor Meyer Memorial Lecture, T., 169 ; P,, 1900, 33. - Presidential Address, T., 555 ; Y. ,‘ - progress of chemistry in Great Britain and Ireland during the 19th century, T., 562.Tiemann, Johann Karl Wilhelm Ferdi- nund, obituary notice of, T., 600. 1900, 77. U. See Pred H. Howles. Udall, William. W, Waage, Peter, obituary notice of, T., 591. Wade, John, the constitution of hydro- gen cyanide, P., 1900, 156. Walker, C. See William Hewry Per- kin, jun. Walker, Jumes, the constitution of cani- phoric acid, T., 390 ; P., 1900, 60. - estimation of atmospheric carbon dioxide, T., 1110; P., 1900, 164. Walker, James, and William Cormack, the dissociation constants of very weak acids, T., 5 ; P., 1899,208 ; dis- cussion, P., 208. -- campholytic and isolauronolic acids, T., 374 ; P., 1900, 58. Walker, James, and Johlz K. Wood, preparation and properties of solid ammonium cyanate, T., 21 ; P., 1899, 209. -- configuration of the camphoric acids, T., 383 ; P., 1900, 59. Warington, Robert, recent researches on nitrification, P., 1900, 65. Watson, Dauid, obituary notice of, T., 603. Wechsler, EJkan. See Raphael Hela dola. West, CL arles AIfred, the dissociation constant of azoimide (hyclrazoic acid), T., 705 ; P., 1900, 74. West, John H. See Thomas Martin Lowry. Whiteley, Martha Annie, the oxime of inesoxamide and some allied com- pounds, T., 1040; P., 1900, 145. Nilliams, P. See Harry Medforth Dawson. Yilliams, Willianz Arthur. See Baphael Xeldola. Vitham, Ernest. See Gewge Young. Vood, John K. ilood, Thomas Barlow. See Richard See James Walker. Hulibzcrton Adie,1342 INDEX OF AUTHORS. Y. Yates, J. See Alexnncler William Gil- body, and William Henry Perkin, jun. Young, George, ana Ernest Witham, C-derivatives of hydroxytrinzole, T., 224 ; P,, 1900, 5. -- hydrolysis of semicarbazones, Young, Sydney, vapour pressures, specific vo!umes, and critical constants of n-octane, T., 1145 ; P., 1900, 166. P., 1900, 73. Young, Sydney, and Emily C. Fortey, note on the refraction and maglietic rotation of hexaniethylenc, chloro- hexsmethylene, a i d dichlorohexa- methylene, T., 372 ; P., 1900, 44. -- vap0u.r pressures, specific volumes, and critical constants of diisopropyl and diisobutyl, T., 1126 ; P., 1900, 165. Young, William J. See Jocelyn Field Thorpe.

ISSN:0368-1645    

DOI:10.1039/CT9007701335

出版商:RSC    

年代:1900

数据来源: RSC

摘要:

1NDEX OF STJBJECTS. TRANSACTIONS. 1900. (hIwked T.); and also t o Proceedings of tlie Session 1899-1900, Nos. 213 to 226, Nov., 1899--June, 1900 (marked P.). A Acacetin from Eobiii irc Pseiitlccccicicc aiiJ its acetj.1 derivative (PEIXIS), T., 430 ; P., 1900, 45. Acetaldoxime, spectruni of (HAI~TLEY and Docem), T., 321; P., 1900, 14. Ac?tanilide, action of dry silver oxide and ethyl iodide 011 (Lasum:), T., $37 ; P., 1900, 6, 90. u - ~ILOILO- a i d 2:4-rZi-bromo- and -cliloro-, formation of ( CHATTAWAY and ORTOS), T., 79s; P., 1900, 112. tii-chloro-, action of bleaching powder 011 a hot acetic acid solution of ( CHLL’TThWAY, ORTUX, and HTRT- LEY), rr., 804. substituted nitrogen chlorides from, and their transformation (CHATT- AWAY, OI~TON, ant1 HURTLET), T., 800 ; P., 1900, 125.( l l - , tri-, and tetra-chloro-derivatives of, from substituted nitrogen chlorides (CHATTAWAY, O ~ r o s , and HURT- LEY), T., 800; P., 1900, 125. Acetanisidide, dinitro- (MELDOLA and ~YECHSLER), T., 1172; l’., 1900, AcAh acid, cyano-, ethyl ester, con- stitution of tlie sodium deriva- tive of (THOILPE), T., 923 ; P., 1900, 113. condensation of the sodium deriv- ative of, with ethyl B-isopropyl- acrylate, and with ethyl a- and P-methylacrylates (HOWLES, TIIOKPE, and UDALL), T., 943 ; P.; 1900, 115. 167. Acetic acid, cyano-, ethyl estw, iotlo- and bromo-derivatives of (THOILIT and YUUSG), T., 9 3 6 ; P., 1900, 115. Acetoacetic acid, ethyl ester, constitution of, and action of dry silver oxide and ethyl iodide, and dry silver oxide and ethyl iocloacetate on (LANDER), T., 738 ; P., 1900, 6, 90.l-Acetonaphthalide, 2 : 4dinitro-, action of tin and of iron on (MELDOLA and Eusos), T., 1159; P., 1900, 166. Acetonedicarboxylic acid, oxidation of, in presence of ferrous salts (FESTOS and JOKES), T., 76 ; P., 1899, 224. trimethyl ester, condensation of, to trimethyl orcinoltricarboxylate (DOOTSON), T. , 1196 ; P., 1900,170. Acetotoluidides, o- and p - , substituted nitrogen chlorides and bromides from (CHATTAWAY and ORTOY), T., 789 ; Acetoxime, spectra of (HARTLEP and DOBBIE), T., 321 ; P., 1900, 14. Acetylaconitic acid, ethyl ester (RUIIE- MASK and STAPLETON), T., 804 ; P., Acetylbenzoyl-i-diphenylethylenedi- amine (JAW and MOIR), T., 612 ; P., 1899, 211. Acetyl-chloro- and -bromo-aminobenz- enes (phenyll acetyl nitrogen chlorides and bromides), and their chloro- and bromo-derivatives, transformation of (CHATTAWAT and OHTOX), T., 798 ; P., 1900, 112.Acetylchloroamino-nzo?zo-, -di-, and -t~i- chlorobenzenes (chlorophelzyl acety2 ni- and HUR‘I’LEY), T., 800 ; P., 1900, 125. P., 1900, 102. 1900, 121. tr’0gCn ChlOTidCS) (CHATTAWAY, OICL‘ON,1344 INDEX OF sur:JEcrs. \ -- BODY, PERKIN, aGd YATEX), P., 1900, 106. C,,H,O,, and C18H3405, from the fusion of dihydroxystearic acid with pot- Acetyl-chloro- and -bromo-aminotolu enes, o- and p - (o- and p-toZyZ acety, ititrogcn chlorides and bro?i~irErs) ani their chloro- and bromo-derivative: .I and alkyl fialoids ( L A N D ~ ~ : ) , T., 729 ; Y., 1900, 6, 90. Aluminium chloride, action of, on cani- phoric anhydride (LEES and PEK- (CHATTAWAY and ORros), T., i90 ; P.: 1900, 102.Acetylchloromorphide (SCIIILTYEH and LEES), T., 1024 ; P., 1900, 143. Acetylenedicarboxylic acid, oxidatioii of, in presence of ferrous salts (FEXTON and JOXES), T., 76 ; P., 1899, 244. Acetylenedicarboxylic acid, ethyl ester, preparation of (RUHEMAHN and condensation of, with &ketonic esters and with benzdmidine and with guaiiidine (RUHEMANN and STAPLETON), T., 804 ; P., 1900, 121. action of phenols on (RUHEMANN and BEDDOW), T., 1119; P., 1900, 165. condensation of, with plieiiyl iner- captan (RUHEMANX and STAPLE- TON), T., 1181 ; P., 1900, 168. Acetylpropionylsalicylic acid osazoiie (AUDEN), P., 1899, 231. Acetyltartaric acid, diethyl ester, rota- tion of (MCCRAE and Pmmnson.), T., 1096 ; P., 1900, 161. Acid, C7H,,0J,.from the oxidation of isopilocarpiiie with perinanganate (JOWETT), T., 852; P., 1900, 124. C9H1,0, (two), from the hydrolysis of methyl bromodihydro-+-lanronolate (LEES and PERKIS), P., 1900, 19. CSH,,BrO, (two), from the action of hydrogen bromide in glacial acetic acid on +-campholmtone (LEES and PERKIN), P., 1900, 18. $H,,O, (two), from the action of alkalis on +-campholactoiie (LEES and PERKIN), P., 1900, 18. C,,H,,O,, from u-clibromocamyhor and nitric acid (LAPWORTH and CHAP- NAN), T., 310 ; P., 1900, 4. from the oxidation of tetramethyl- hmiatoxylin (PERKIN and YATES): P., 1900, 108. C1lHIGOJ, and Cl,Hl,O,, from the action of hydrogen cyanide and hydro- chloric acid on camphonic acid ( LAPWORTH and CHAPMAN), T., 450; P., 1900, 56. C,,H,,O,. and C,,,H,.O,.from tlie oxid- BEDDOW), 'r., 1121. C11H1207, C!XIH200w c20H20010? Acids froni ethyl uyanoacetate, niethod of sepnrating the cis and tmns- modifications of (THOIWE), T., 934 ; l'., 1900, 114. fatty, determination of the coiistitn- tion of (CROSSLEY a i d LE SUEUR), T., 83 ; P., 1899, 225. ilibasic, dissociation constants of ( W~LICER), T., 397. iiiorgaiiic, very weak, dissociation coii- stants of (WALKEF. and C'O~~MACK), T.,.5 ; P., 1899, 208. orgnnic, oxidation of, in presence of' ferrous salts (FENTOW and JOSES), T., 69 ; P., 1899, 224. Aconite alkaloids (DUNSTAN and READ), T., 45 ; P., 1899, 206. Aco?~itzcm Nn;UeZZ.us, comparison of the properties of tlie alkaloids from, with those from Japanese aconite (DUNSTAN and READ), T., 63. Acroses, U- a i d B-, from glycollic alde- hyde (JACKSOX), T., 129; P., 1899, 238.Address, presidential (TILoI:I)I~:), T., Aldehydes, compounds of, with iso- cyanides (WADE), P., 1900, 157. aromatic, condensation of, with azodi- carbdmide (YOUNG aud M 7 1 ~ ~ ~ n 1 ) , T., 224 ; P., 1900, 5. action of, 011 derivatives of B-naphth- ylamine (MORGAN), T., 1210 ; Aldehydo-o-aminobenzoic acid, plienyl- hydrazone and semicarbazone of (ELLIOTT), T., 214 ; P., 1899, 243. Alkali nitrites, coloiir of (DIVERS), P., 1900, 40. Blkalis, action of iodine 011 (TAYLOR), T., 725 ; P., 1900, 70. Slkaloids of Japanese aconite and of Acoititum ATapellzcs, comparison of properties of (DUNSTAS and READ), T., 63. of jaboraiidi leaves (JuwE~T), T., 473 ; P., 1900, 49. Ukyl iodides and dry silver oxide, alkylation by means of (LAKDEK), T., 736 ; P., 1900, 6, 90.action of, on incrcuric iotlide-sulph- ides of the fatty seiies (SMILES), T., 160 ; P., 1899, 240. compounds of, with isocyaiiides 555 : P., 1900, 77. ' Y., 1900,171. (WADE). P.. 1900. 157. I1 1- " I L.7 I" "l ation of trimethvlbrazilin (GTT.- I Alkvlstion b; ;uea;is of drv silver oxideINDEX OF SUBJECTS. 1345 Amides, action of dry sil vcr oxide aiid alkyl iodides on (LANDEK), 'l'., 736 ; P., 1900, 6, 90. Anhydro-cis-pentamethylene tricarb- oxylic acid (BOTTOMLEY aiid PEILKIN), 'l'., 304 ; P., 1900, 16. Amidosulphite, forination and decoin- position of (DIVERS and Ocawa:, 'l'. , 327 ; P., 1900, 38. Amidosulphuric acid, production of (DITEIS alla H,~G~L), T., 97s ; P., Ammonia, spectra of (HAWTLEY and DOBBIE), T., 318 ; P., 1900, 14.electrolysis of (SZARVASY), T., ti04 ; P., 1900, 3. solubility of aqueous, in potassium car- bonate solution (NEWTH), T., 775 ; P., 1900, 87. distribution of, between chloroform and water (Dawsos and MCCRAE), 'l'. , 1242; P., 1900, 172. action of dry sulphur dioxidc on dry (DIVERS and OGAWA), T.. 3 2 7 ; Y., 1900, 38 ; (DIVERS), P., 1900, 104. influence of, on the action of nitrifying organisms (WAIXNGTOS), P., 1900, 6 6. Ammonium hydroxinIidosuli)hate, yro- ductioii of (DIVERS and HAGA), T., 689; P., 1900, 71. tliiosulphate, prepamtion of, aiitl action of heat on (DIVERS and Ocawn), aniidosulphite, forination and decom- position of (DIVEIS and O c a w ~ ) , T., 237 ; P., 1900, 38. imidosnlpliite (DIVERS aiid Oc.iwa), P., 1900, 113.snlphites, preparation of, and action of heat on (DIVERS and OGAWA), T., 335 ; P., 1900, 39. trithionate, preparation of, and action of lieat on (DIVERS and OGAWA), T., 335 ; P., 1900, 39. Ammonium organic compounds :- Ammonium cyanate, solid, prepaiatioii aiid lwoperties of (W.hLiim and WOOD), T., 21 ; P., 1899, 209. cynnates, substituted, transformation of (WALKEP, and WOOD), T., 33 ; P., 1899, 209. Amy1 snlphide-mercuiic iodide (SmLes), isoAmylcitraconic acid (LAWRENCE), LsuAmylsuccinic acid, iiieltiiig point of 1900, 147. T., 335 ; P., 1900, 39. T., 164 ; P., 1899, 240. l'., 1900, 156. (LAWREXCE), P., 1900, 156. Anilides, action of hypochlorons aiid liypobromous acids on (CHAT i AWAY and ORI'OS), T., 134, 789, 797 ; P., 1899, 232; P., 1900, 102, 112; (CIIAwAwAY, OKTOX, and Hum- LEY), T., 800 ; p., 1900, 125 ; (AI~M- substitution in (ARMSIROSG), T., 104'7 ; P., 1900, 160.Aniline aiid its hydrochloride, elcctro- lysis of fused mixtures of (Sz~rn- VBSY), T., 208; P., 1899, 194. iiieta-sulphonation of (ARMSTROW ancl BEILRY), P., 1900, 159. Anilinoinduline, B,, 4, electrolytic pre- para tion of (SZM:VASY), T., 307 ; p., 1899, 194. Anisidine, tlinitro-, diszotisatioii of (N ELDOLLA and WECIISLER), T., 1172 ; P., 1900, 167. Annual General Meeting, T., 555; P., Anthranilic acid (o-nr)~ir~obo~:oic ( w i d ) , action of chloroforin and potash 011 (ELLIOTI'), T., 213 ; P., 1899, 243. Apigenin and Apiin, action of nitric acid on (PERKIX), T., 116; l'., 1900, 44. Apigetrin, and nitro- (PERKIN), T., 420; P., 1900, 45. drctostnphglos Uua-icwi, constituents of (PERKIN), T., 424; P., 1900, 45.Arsenic, new snlphide of (AS.$) (SCOTT), T., 651 ; P., 1900, 69. Atmospheric air, estimation of carbon dioxide in (WALKER), T., 1110; P., 1900, 164. Atomic weight of nitrogen (DEAs), T., 117; P., 1899, 213. Azines, formation of, by the decompo- sition of semicarbazones ( KIPPINU), P., 1900, 64 ; (Yovsc and WITHAM), P., 1900, 73. Azo-compounds differentiated front hydr- azone compounds by bromine (ARM- Azodicarbamide, condensation of, with aromatic aldehydes (YOVSG atid WITHAM), T., 224 ; P., 1900, 5. Azoimide, electrolysis of ( SZARVASY), dissociation constant of ( WES r), T., SrROSG), T., 1047 ; p., 1900, 160. 1900, 77. STIZOSG), P., 1899, 243. T., 606; P., 1900, 3. 705; P., 1900, 74.1346 INDEX O F SURJECTS.Azophenine, electrolytic preptrat,ion of (SZARVASY), T., 207; P., 1899, 194. B. Balance Sheet of the Clieinical Society, March, 1900, and of the Research Fund, March, 1900. See Annual General Aleeting, T., 588. Barium chlorate, decomposition products of (SODEAU), T., 137; P., 1899, 157. hydroximidosulphate, production of (DIvms and HAGA), T., 690 ; P., 1900, 71. Benzal-. See Benzylidene-. Benzaldehyde, actiou of, on ethyl-B- iiaphthylaniine (MORGAN), T., 1210 ; P., 1900, 171. action of dry silver oxide aiid ethyl iodide on (LANDEK), T., 746. Benzaldoximee, nati- and s p , curves of the molecular vibrations of ( HAISLEY and DOBBIE), T., 509 ; P., 1900, 55. Benzamide, action of dry silver oxide ";"d ethyl iodide on (LAXDE~L) T., t 3 6 ; Y., 1900, 6. hcrcachloride, preparation and proper- 1900, 176.Benzamidine, condensation of, with the ethyl esters of acetylenedicarboxylic and chlorofumaric acids (RUHEMANS and STAPLETON), T., 809 ; P., 1900, 122. action of, on ethyl phenylpropiolate ties of (hiATTHEWY), T., 1275 ; P., (kJHElMANK and STAPLETON), T., 239 ; P., 1900, 11. o-bromo- aiid -chloro-, nitrogen brom- ides and chlorides from (CHATTAwBY and ORTON), T., 800. Benzene, refraction and magnetic rota- tion of (PEBKIK), T., 267; P., 1899, 237. chloro-, tetrachloride, preparation of (MATTHEWS), T., 1276 ; P., 1900, 176. Benzeneazo-o-dzlromophenol, its acyl de- rivatives and ethyl ether ( HEWITT and ASTON), T., 712; P., 1900, 89. p-bronio-, and its acyl derivatives and ethyl ether (HEWITT and ASTON), T., 810 ; P., 1900, 131.Benzeneazoethyl-B-naphthylamine, p - nitro- (MORGAN), T., 1214. Benzeneazo-o-nitrophenol, preparation, properties, and reactions of, and its acetyl and benzoyl derivatives (HEWITI), T., 99; P., 1899, 229. Benzanilide (SILBEBRAD), 1'. , 11 91. Benzeneazophenol, brominatioii of (HEwI'rr and ASTON), T., 712, 810 ; P., 1900, 89, 131. nitration of (HEWITT), T., 99 ; P., 1899, 229. Benzeneazophenol, p-nitro- and its acetyl aiid benzoyl derivatives, and p-amino-, aid its acetyl derivatives (MELDOLA and WILLIAMS), P., 1899, 196. Benzene-o-disulphonic acid and its salts arid derivatives (ARMSTRONG and NAPPEIL), P., 1900, 160. Benzenoid hydrocarbons, refractive and magnetic rotatioii of (PISKKIS), T., 267; P., 1899, 237. Benzoic acid, oxidation of, in presence of ferrous salts (FEsrrox and JOSES), T., 76 ; P., 1899, 224.hexnchloride, preparation of (MAT- THEWS), T., 1276; P., 1900, 176. Benzoic acid, o-amino-. See Anthranilic acid. na-nitro-, ethyl ester, chloro- a i d bromo-iniide of (STIEGLITZ and SLOSSON), P., 1900, 2. Benzoic chloride, action of, on s-3:6-tli- niethyldihydrotetrazine (SILmait2ii)), T., 1185 ; P., 1900, 169. Benzoin, action of dry silver oxide and alkyl iodides on (LANDER), T., 733; P., 1900, 6, 90. Benzonitrile Jvxachloride, preparation and properties of (MATTHEWS), T., 1273 ; P., 1900, 175. Benzo-y-pyrone ant1 its carboxylic acid (RUHEMANX and S~APLETON), T., 1180 ; P., 1900, 168. Benzoylacetic acid (R~HEMANN and STAPLETON), T., 1180; P., 1900, 168. Benzoylaconitic acid, ethyl ester of (RUHEMANN and STAPLETON), T., 804 ; P., 1900, 121.Benzoyl-s-dibenzyl-i-diphenylethylene- diamine (" di6enzyZn~nurinc 'I) (JAPP and MOIR), T., 608 ; P., 1899, 211. Benzoyl-s-dimethyl- and -s-diethyl-i-di; phenylethylenediamine ( " dimetJ~yZ- aiid ' ' diethyl-amarine ") ( JAPP aiitl MOIIL), T., 608; P., 1899, 211. aa-Benzoylphenylhydrazide, action of heat on (SILBERKAD), T., 1190; Y . , 1900, 169. Benzylanilinesulphonic acids (SbIED- LEY), I?., 1900, 160. Benzylideneazine, formation of (Y ouxa and WrTwm), P., 1900, 73. Benzylidenehydantoin and Benzylidene- imino- and -thio-hydantoin (RUHE- MANN and STAPLETOX), T., 241 ; P. 1900, 12.ZNDEX OF SUBJECTS. 1347 Benzylidene-2-naphthylamine, 1 -bromo - and 1 -chIoro-, and their hydrocyanides and a- and p-nitro-derivatives (h1or:- GAY), T., 1216; P., 1900, 171.Benzylideneneobornylamine ( FORSTER and HART-SMITH), T., 1157 ; P., 1900, 166. Benzylidenephenylhydrazone ( MOE- GART), T., 1210. Benzylidenesemicarbazone, oxidation of Bismuth snlphates (ADIE), P., 1899, 226. Boric acid, dissociation constant of (WALKER and CORMACR), T., 16 ; P., 1899, 208. Bornylamine salts, and their molecular rotation (FOESTER and HAw-Sarrm), 'l'., 1152 ; P., 1900, 166. 8-Bornylhydroxylamine (1-hydroxyl- crminocnniphnne) (FORSTEE), T. , 255 ; P., 1900, 14. Bornyloxamide ( FORSTER and Hanr- Brazilin ( GILBODY and PEPKIN), P., 1899, 241. constitntion of (GILBODY, PERKIS, and YATES), P., 1900, 107. Butanedicarboxylic acids. See :- Diinethylsuccinic acid. Methylglutaric acids. cycZoButanedicarboxylic acid (cis-tetm- iizethy7ene-1: 3-dicnTbozylic acid), forniation of ( BOTTOMLEY and PER- MX), T., 306 ; P., 1900, 16.Butanetetracarboxylic acid, a6-di- bromo-, ethyl ester (LEAN), T., 103 ; P., 1899, 197. wButyl isocyanide (WADE), P., 1900, 157. isoButylbenzene, preparation and pro- perties of (PERKIS), T., 268 ; p., 1899, 237. isoButyric acid, a-bromo-, ethyl ester, condensation of, with ethyl malonates and ethyl cyaiioacetatcs ( LAWREWE), P., 1900, 154. (YOVSG alld WITIIAhf), T., 226 ; P., 1900, 5. SMITH), T., 1155 ; P., 1900, 166. C. Cadmium iodide, combination of, with ammonia in aqueous solution (D,4w~ SON and MCCKAE), T., 1246 ; P., 1900, 173. Calcium chloride, combination of, with ammonia in aqueous solution (Daw- SON and McCK~E), T., 1249 ; P., 1900, 173. hydroxirnidosulphate, production of (DIVERS and HAGA), T., 690; P., 1900, 71.Camphane, 1-nitro-, +-nitro- and its potassium and benzoyl derivatives, 1:l-bromonitro-, 1:l-chloronitro-, and 1:l-iodonitro- (FORSTER), T., 251 ; P., 1900, 13. Camphanic acid, isomeride of ( PERKIN and THOBPE), P., 1900, 152. 4-Campholactone and its isomeride (LEES and PERKIK), P., 1900, 18. Campholide, a-bromo-, its formula and hydrolysis ( LAPWORTH and CHAP- MAN), T., 446 ; P., 1900, 56. dibromo- (LAPwoRrH and CHAPMAI\'), T., 310 ; P., 1900, 4. Campholytic acid and its stereoisomerid?, reactions and structure of (WALKER and CoRarAcIc), T., 374 ; P., 1900, 58. Camphonic acid, its oxime, semicarh- azone, and phenylhydrazones, a d action of bromine and of hydropl cyanide on (LAPWOKTH and CH-IP- Camphonolactone, ~rzm~o- and tri-bronio- (LAPWORTH and CHAPMAN), T., 446 ; P., 1900, 56.Camphononic acid, formation of (L.4r- WOR'I'H), T., 1070. action of bromine and hydrogen cyanide on, and its oxinie (LAP- WORTH and CHAPMAS), T., 452 ; Camphopyric acid a i d anhydride bronio-derivatives of (G~RDNER), P., 1900, 46. Camphor, constitution of (LAPWORTH), vapour pressure of (ALLEN), T., 413 ; P., 1899, 135. Camphor, a-dibromo-, action of fuming nitric acid on (LAPWOKTH and aa'-bromonitro- ( LAPWORTH and CHAPMAN), T., 310 ; P., 1900, 4. cyano-, and its chloro- and bromo- derivatives and their hydrolysis 128. Camphorenic acid, bromo-, formula of (LAPWORTH and CHAPMAN), T., 446 ; P., 1900, 56. Camphoric acid, constitution of (WALKER), T., 390 ; P., 1900, 60. experiments on the synthesis of (PERKIN and THORI'E), P., 1900, 152.Z-isocamphoric acid and its ethyl esters (WALKER and WOOD), T., 3S3 ; P., 1900, 59. Camphoric acids, configuration of (WALKER and WOOD), T., 383 ; P., 1900, 59 ; (WALKER), T., 395 ; P., 1900, 61. MAS), 'r., 446 ; P., 1900, 56. P., 1900, 57. lr., 1053 ; P., 1900, 128. CHAPMA4X), T., 309 ; P., 1900, 4. (LAPWORTH), rr., 1053 ; P., 1900,1348 INDEX OF SUBJECTS. Camphoric anhydride, action of alumin- ium chlcride on (LEES and PERKIN), Camphoronic acid, formation of (LAP- WORTH), T., 1071. Camphoroximeacetic acid and its sodium and bornylamine salts ( FOI~STER and 166. P., 1900, 18. HART-SMITH), T., 1154 ; P., 1900, Cane-sugar. See Sucrose. Carbamide (uren), rate of formation of, from solid ammonium cyanate (WALKER and WOOD), T., 30 ; P., 1899, 209.Carbohydrates, action of hydrogen Deroxide on, in Dresence of ferrous salts (MORRELL and CROFTS), T., 1219 ; P., 1900, 171. Carbon monoxide (carbonic oxide) and oxygen, influence of the nascent state on the combination of dry (RUSSELL), T., 361 ; P., 1900, 42. dioxide (carbonic anhydride), dissocia- tion constant of (WALKER and CORMACK), T., 8 ; P., 1899, 208. estimation of, in the atmosphere (WALKER), T., 1110 ; P., 1900, 164. disulphide, estimation of (RUSSELL), Carbonyl sulphide, estimation of (Rus- SELL), T., 356; P., 1900, 41. Catecholacetic acid (o-hydrozyphen- ozyncetic acid), and its ethyl ester, anhydride and anilide (CARTER and 152. Chemical constitution and fluorescence (HEWITT and PERKIXS), T., 1324 ; P., 1900, 178; (HEWITT), P., equilibrium between hydrogen per- oxide and “ persulphuric acid ” (LOWRY and WEST), T., 955 ; P., 1900, 127, Chemistry, progress of, in Great Britain and Ireland during the 19th century (THORPE), T., 562.Chlorates, decomposition of (SODEAU), T., 137, 717; P., 1899, 157; 1900, 88. Chlorine, evolution of, from chlorates T., 359 ; P., 1900, 41. LA4WREKCE), T., 1222 ; P., 1900, 1900, 3. (SODEaU), T., 137, 717 ; P., 1899, 157 ; 1900, 88. amount of, in rain-water collected a t Cirencester (KINCH), T., 1271 ; P., 1900, 183. Chlorophyll, chemistry of (MARCH- LEWSKI and SCHUNCK), T., 1080; P., 1900, 148. Chrysoidine hydrochloride, bromo. and chloro- (MORGAN), T., 1205 ; P., 1900, 170. Chrysoidinesulphonic acid, chloro- and bromo-, potassium salts of (MORGAN), T., 1205.Cinnamal-. See Cinnamylidene-. Cinnamylidene-2-naphthylamine, 1 - bromo- and l-chloro-, and their hydro- cyanides (MOEGAS), T., 1217; P., 1900, 171. Cinnamslidenesemicarbazone, oxidation of (Y~USG and WITHAM), T:, 230 ; P., 1900, 5. Citrazinic acid, coiistitution of (SELL and Cobalt nitrite, double potassium and sodium salt of (ADIE and WOOD), T., 1076; P., 1900, 17. oxides, hydrated, green- and buff- coloured (HARTLEY), P., 1899, 202. potassium sulphate (MALLET), T., 222; P., 1899, 227. Colour of alkali nitrites (DIVEIS), P., Colouring matters of Arctostaphylos Uvn- w s i , Coriarin myrtifolin, Hcenzn- toxylm cn?npechiantcm, Myrica Gale, B~LZCS i!Ietopium, and Robinia Pseud- nccccin (PERKIN), T., 423 ; P., 1900, 45. of chlorophyll and their spectra (MARCHLEWSKI and SCHUNCK), T., 1080 ; P., 1900, 148.Copper, heat of combination of, with zinc (BAKEIL), P., 1899, 195. Copper chloride, combination of, with ammonia in aqueous solution ( DAW- SON and NCCRAE), T., 1245 ; P., oxide, combination of, with ammonia in aqueous solution (Dawsox and McCns~), T., 1255 ; P., 1900, 173. snlphate, combination of, with ammo- nia in aqueous solution (DAWSON and McCnilE), T.,11243; P., 1900, 172. reaction of solutions of, with mag- nesium, iron, or zinc (CAVEY), P., 1899, 232. sulphovanadite. See Sulvanite. Corinria myrtifolia, constituents of (PERKIN), T., 428; P., 1900, 45. Cresols, o-, m-, and p-, condensation of, with ethyl phenylpropiolate (RUHE- MANN and BEDDOW), T., 984, 1119 ; P., 1900, 123, 165. Iresoxy-. See Tolyloxy-.Jritical constants of diisopropyl and diisobutyl (YOUNG and FORTEY), T., 1126; P., 1900, 165. DOOTSON), T., 233 ; P., 1900, 9. 1900, 40. 1900, 172.INDEX O F SUBJECTS. 1349 Critical constants of n-octane (YOUNG), T., 1145 ; P., 1900, 166. Crotonic acid, ethyl estrr, condensation of, with ethyl oxalate (lAAI’WORTIf), Crystallography of d - and I-isoxmarine (Pope), T., 787 ; P., 1900, 119. q-Cumene (1 :3:4-t,.ieth?JIDciz=ene), refrac- tion and inagiletic rotation of (PEIL- ICIS), T., 267 ; P., 1899, 237. Cuminylidene-2-naphthylamine, 1- bromo- and 1-chloro-, and their hydro- cyanides (XIORGAN), T., 1216 ; €’., 1900, 171. isocyanides, compoiinds of, with alde- hydes and slkyl iodides (WADE), P., 1900, 157. Cymene (1 :4-ntetl~~liso~,rop~Zbe?zrelze) re- fraction ancl magnetic rotation of (PERKIN), T., 267 ; P., 1899, 237.I?., 1900, 132. D. Dehydracetic acid (COLLIE), T., 971 ; P. , 1900, 147. Dehydrocamphoric acid, formation and oxidation of (LIPWORTH), T., 1056 ; Density of the halogens, nitrogen and oxygen a t their boiling points (DRUGMAX and RAMSAP), T., 1228; P., 1900, 172. Deoxybenzoin benzylideneanilines and their hydrochlorides, isomeric ( F ~ a x - CIS), T., 1191 ; P., 1900, 169. Deoxymorphine (SCHRTVER and LEES), Dextrose (d-glzccose, g r i y e sugnr), action of potassium persulphate on (MOREELL and CROFTS), T., 1220 ; P., 1900, 172. Diacetylacetone, action of iiiethyl iodide on the sodium derivative of, and orcinol derivatives froin (COLLIE and STEELE), T., 961 ; P., 1900, 146. Diacetyltartaric acid, diethyl ester, rotation of (MCCRAE and PATTERSON), T., 1096 ; P., 1900, 161.Diacylamarines, constitution of (JAPP and ~ ~ o I R ) , T., 632 ; P., 1899, 212. Dialkylamaronium salts, constitntion of (JAPP ancl ~IoIR), T., 615 ; P., 1899, 212. Diazosalicylic acid and chloride and sulphonic acid (AUDEN), P., 1899, 231. Diazotisation, elimination of a nitro- group during (MELDOLA and WECH- SLER), T., 1172; P., 1900, 167. Dibenzoyl-s-dibenzyl-i-diphenylethyl- enediamine ( J A W and ~ ~ o I R ) , T., 608 ; P., 1899, 211. P., 1900, 128. rr., 1024 ; P., 1900, 143. s-Dibenzoyl-i-diphenyle thylenediamine (JAPP and MOIR), T., 611 ; P., 1899, 211. s-Dibenzoylhydrazide (SII~BER~AD), T., 11% ; P., 1900, 169. Dibenzoylsuccinic acid, ethyl esters, nbsor1)tion curves of (HARTLEY and Dibenzyl wlphide-mercnric iodide (SMILIX), T., 164 ; P., 1899, 240.“ Dibenzylamarine.” See Benzoyl-s- dibenzyl-i-diphenylethyleiiedianiine. s-Dibenzyl-i-diphenylethylenediamine (JAPP and MOIR), T., 610 ; P., 1899, 211. Dibenzyl ketone benzylideneanilines and their hydrochlorides, isomeric (F~ascrs), T., 1191 ; P., 1900, 169. Dibenzyllophonium chloride (JAPP and Dibenzyl-B-naphthylamine, and the action of forinaldehyde on (MORGAN), T., 825; P., 1900, 131. Dibornyloxamide (FORSTER and HART- SMITH), T., 1152; P., 1900, 166. Diisobutyl. See Octane. s-Diisobutylsuccinic acids, cis- and trans-, preparation and dissociation constants of (BOSE and SPRASKLISG), T., 1299 ; P., 1900, 184. Diethyl sulphide-mercuric iodide (SMILES), T., 164 ; P., 1899, 240. 2:2 -Diethyldiamino-1:l’dnaphthyl- methane, and its dibenzoyl deriva- tive (MORGAK), T., 827 ; P., 1900, 131.Diethyl-a- and -B-naphthylamines, and the action of formaldehyde on (Mort- GAN), T., 823 ; P., 1900, 131. Diethyltetrahy dro-P-naphthylamine, action of formaldehyde on (MORGAN), T., 824. Dihydroxybutanetetracarboxylic acid, and its 8-lactone (LEAS), T., 10.1, 108 ; P., 1899, 197. Dihydroxylamine derivatives, non-exist- ence of (DIVERS and HMA), T., 437 ; P., 1900, 5-1. Dihydroxylaminesulphonates, non- existence of (DIVERS and H a n ~ ) , T., 437 ; P., 1900, 54. 26-Dihydroxyp yridine-4-carboxylic acid. See Citrazinic acid. 2:6-Dihydroxypyridine-3:4-dicarboxylic acid, ethyl ester (RUHEMANX and STAPLETON), T., 243; P., 1900, 12. Dihydroxystearic acid, action of fused potash on (LE SUEUR), P., 1900, 91.Dimethyl sulphide-mercuric iodide (SMILES), T., 164 ; P., 1899, 240. ‘ I Dimethylamarine.” See Renzoyl-s- dimethyl-i-diphenyle t hylenediainine. DOTME), rr., 49s ; P., 1900, 57. JIOIR), l’., 614; P., 1899, 212.1350 INDEX OF SUBJECTS. aa-Dimethyl-a,-isoamylsuccinic acid, pre- paration and dissociation constant of (BOSE and SPRASKLIRG), T., 1306 ; P., 1900, 184. Dimethylbutanetricarboxylic acid, ethyl ester, action of sodium aud methyl iodide on (PERKIN and THORPE), P., 1900, 152. aa-Dimethyl-a,-isobutylsnccinic acid, and its a’-cyano-derivative (LAW- RENCE), P., 1900, 155. preparation and dissociation constant of (BONE and SPRASKLING), T., 1304 ; P., 1900, 184. Dimethyldiacetylacetone (COLLIE aiid STEELE), T., 961 ; P., 1900, 146.s-3:6-Dimethyldihydro- 1 :2:4:5- tetrazine and the action of heat and of benzoic chloride on (SILBERRAD), T., 1185 ; P., 1900, 169. aa-Dimethyl-a,-ethylsuccinic acid, pre- paration and dissociation constant of (BONE and SPRANKIJNG), T., 1305; P., 1900, 184. Dimethylethylsulphine iodide mercuric iodide (SMILES), T., 162, 1 6 7 ; P., 1899, 240. ad-Dimethylglataric acids (peq~tnne- dicurbozglic acids) (THORPE), T., 933 ; (HOWLES, TIIOKPE, UDALI,, and NEALE), T., 948 ; P., 1900, 116. BB-Dimethylglutaric acid (pentaitc- dicnrboxglic acid), ad-clibromo-, ethyl ester, condensation of, with ethyl sodiomalonate (PERKIN, THOKPE, and WALKER), P., 1900, 149. Dimethylcyclohexanecarboxylic acid (hexalzydroxylic acid) and its isomer- ide (LEES and PEI~KIS), P., 1900, 20.Dimethyl-a- and -8-naphthylamines and the action of formaldehyde on (MORGAS), T., 822; P., 1900, 131. aa-Dimethyl-a,-n- and -iwpropyl- succinic acids, preparation a i d dis- sociation constant of (BONE and 184. 2:5-Dimethylpyrazine, absorption spec- trum of (HARTLEY and DOBBIE), T., 846 ; P., 1900, 129. Dimethylpyrone, action of sodium ethoxide on (COLLIE and STEELE), T., 970 ; P., 1900, 146. action of iodine on the barium and sodium salts of, and its periodide (COLLIE and STEELE), T., 1114; P., 1900, 164. as-Dimethglsuccinic acid and anhydride (PERKIS, THOr:m, and WALKER), 1’. , 1900, 149. SPRAiXIiLING), T., 1305 ; P., 1900, aa-Dimethylsuccinic acids, preparati on and dissociation constants of ( B ~ I S E and SPRANKLING), T., 1204; P., 1900, 184. 3:5-Dimethyl-1:24-triazole, synthesis of, and its hydrochloride and nitrate (SILBEI~RAD), T., 1187; P., 1900, 169.Dimorphism of cyanocamphor and its chloro- and bromo-derivatives (LAI’- WORTII), T., 1059; P., 1900, 128. Diphenacetyltartaric acid, diethyl ester, rotation of (hlCCRAE and PATTEESON), T., 1096 ; P., 1900, 161. as-Diphenoxysuccinic acid, ethyl ester (RUHEhlANK and BEDDOW), T., 1121 ; (RUIIEMAXN and STAPLETOS), T., 1183 ; I’., 1900, 168. Diphenyldiazoxole, preparation and isolation of ( SILBERBAD), T., 1188 ; P., 1900, 169. s-3:6-Diphenyldihydrotetrazine (SIT,- EERRAD), ‘l’., 1188 ; P., 1900, 169. Diphenylethylenediamine, its nitro-de- rivntives, nitrate and mercurichloride (NILLS), T., 1020 ; P., 1900, 127. i-Diphenylethylenediamine (m. p. 120- 121”), action of iiitrous acid on (JAPP and Mom), T., 642.DiphenylFyrimidone (RUHEYANN and Diphenylsuccinic acid, dithio-, ethyl ester (RUHEJIANS and STAYLETON), 3: 5-Diphenyl-1: 2: 4-triazole, preparation and isolation of (SILBERRAD), T. , 1188 ; P., 1900, 169. Diisopropyl. See Hexaue. S-Di-7~- and -iso-propylsuccinic acids, cis- and h n s - (octnneclicnrboxylic acids), preparation mid propcrties of (BOSE aiid SPI?.\NKLING), T., 654; P., 1900, 71. Dissociation constants of alkyl-substi- tuted succinic acids (BOSE and SPRASGLIXG), T., 667, 1298; P., 1900, 72, 184. of normal saturated dibasic acids (WALKER), T., 397. of azoimide (WEST), T:, 705; P. , 1900, i4. of campholytic and isolauronolic acids of cainphoric acid aiid its deriva- tives (WALKER), T., 396 ; P., 1900, 61. of carbon dioxide (WALKER and CORMACK), T., 8 ; P., 1899, 208.of dehydracetic acid ( WALKE~L), 1’. , 971 ; P., 19Q0, 147. of hydrocyanic acid (WALKER and STAYLETOX), T., 239; P., 1900, 11. T., 1183; r., 1900, 168. (WALIiEIt), T., 399. CORhlACK), T., 1 5 ; P., 1899, 208.INDEX OF Di-o-, - / / L - , a d -y-tolylethylenediamines, their nitro-derivatives, nitrates, and niercurichlorides (MILLS), T., 1020 ; P., 1900, 127. E, Elaidic acid, formation of, aid action of dilute nitric acid on (EDMIED), l’., 1899, 190. Electrical conductivity of acids, ap- l’aratus for measuring the P., 1899, 208. of azoimidc (WE~T), T., i 0 7 ; P,, 1900, 73,. Electrolysis of the nitrogen hydrides and of hydroxplarnine (SZ.LKVASY), T., 603 ; P., 1900, 3. of f~isecl mixtures of aniliiie and its Iiydrocliloride (Szanvasr), T., 208 ; P., 1899, 194.Electrolytic dissociation of vcry weak inorganic acids ( WALKEC and Cox- XACK), T., 5 ; P., 1899, 208. preparation of induline dyes (Szilii- Ellagic acid from various taniiiii niattc~ s Equilibrium between hydrogen peroxide and yersulphnric acid ( LOWRY and WEST), T., 9 E i ; I)., 1900, 127. Ethanedicarboxylic acids. See :- Metliylmnlonic acid. Succinic acid. Ethenyll?.iaminonaphthalene and its isomelide and their salts, and acyl-, methyl-, and phenylazo-derivatives (NI~LDOLA and EYSON), T., 1169; l’., 1900, 166. Etherification, inhibiting efyect of, 011 substitution in phenols ( ~ ~ R J I ~ ’ ~ ’ ~ : O S C ; mid LEWIS), P., 1900, 157. of B-naphthol derivatives ( D.L\-Is), T., 33 ; P., 1899, 210. Ethers, formation of, by means of dry silver oxide and alkyl haloids (LASIIEH), T., 729 ; P., 1900, 6, 90.Ethoxycaroaic acid and anhydride (PEiuiIs, THORPE, aiid WALKER), P., 1900, 149. 2-Ethoxypyridine, 3:5:6:4-t?.ichloro- amiiio- (SELL aiid Doorsos), T., 4. Ethyl iodide, action of, 011 mercurous nitrite (RAY), P., 1899, 239. Ethylacetoacetic aoid, ethyl ester, action of dry silver oxide and ethyl iodide on (LANDEB), T., 741 ; P., 1900, 6. Ethylbenzene (phe?~gZetl~n?ze) refraction and magnetic rotation of (PERKIS), T., 267 ; P., 1899, 237. VOL. LXXVII (WALKER :i11d c‘uIihi.iCli), T., 5 ; WY), ‘r., 207 ; Y . , 1899,.194. (l’EIXIS), T., 483. SUBJECTS. 1351 Ethyldiacetylacetone (2) (COLLIE and Ethyl-B-naphthylamine, action of benz- aldehyde on (MORGBS), T., 1210 ; P., 1900, 171.hydrochloride, action of fornialdehyde on (Moncas), T., 828 ; P., 1900, 131. Ethylisopropylacetic acid. See Heptoic acid. Ethylisopropylmalonic acid and its etliyl ester (CEOSsLEY and LE S r E U R ) , T., 83 ; P., 1899, 225. STEELE), ‘r., 970 ; P., 1900, 146. I?. Ferrous cyanide, coiistitution of ( BROWS- ISG), T., 1236; P., 1900, 172. Fluorescein, nitro-derivatives, prepara- tion and constitution of (HEWITT and PECKINS), T., 1324 ; P., 1900, 178. Fluorescence and chcmical constitution (HEWITT and PERKISS), T., 1324 ; P., 1900, 178 ; (HEivITT), P., 1900, 3. Formaldehyde, formation of (PESTON), T., 1297 ; P., 1900, 148. condensation of, with ethyl malonate (BOTTOJILEY and PERKIS), T., 294 ; P., 1900, 16. action of, on aniines of the naphthal- ene series (MORGAN), T., 811 ; P., 1900, 131.Formylanilide, o-bromo- and -chloro-, nitrogen bromides and chlorides from (CIIAITAWAY and ORTOS), T., 800. Fumaric acid, cliloro-, ethyl ester, coii- densation of, with benzamidico and guanidine (RUHEJIASN and STIPLETOS), T., 808 ; P., 1900, 122. action of sodium phenoxidc on ( RL-IIEMASS and UEDDOW), T., 1123 ; P., 1900, 165. Furfuraldehyde, estimation of (COK- Furfurine, an isomeride of (MILLIXUTON IIACIC), ‘y., 990 ; P., 1900, 166. and HIBBEKT), P., 1900, 101. G. Galactose, oxidation of, by hydrogen peroxide (MORRELL and CROFTS), T., 1219. Gas, liquefacticn of a, by “ self-cooling ” (NEWTH), P., 1900, 87. Genistein and its methyl and ethyl ethers and their acetyl derivatives and deconiposition products ( PERKIN and HORSFALL), T., 1310 ; P., 1900, 182.4 z1352 INDEX O F SUBJECTS. cl-Glucose. Set: Dextrose. Olncoeidee from parsley (PERKIN), T. Glutaric acid (n-pyrutarlcwic acid propanedicarbozylic acid), formatior of (BOTTOMLEY and PERKIN), T. 300 ; P., 1900, 16. bromo-, ethyl ester, action of alcoholic potash on (BOWTELL and PEHKIN), P., 1899, 241. Glyceric acid, oxidation of, in presence of fyrons salts ( FENTON and JONES), T., r2 ; P., 1899,224. Glycollic acid, oxidation of, in preseiicc of ferrous salts (FENTOS and JONES), T., 70 ; P., 1899, 224. Glycollic aldehyde, formation of a- and B-acrose from (JACKSON), T., 129 ; P., 1899, 238. degradation of (FEXTON), T., 1294 ; P., 1900, 148. Glycollic aldoxime (FESTON), T., 1296 ; P., 1900, 148. Glycollonitrile, acetyl derivative, pre- paration of, and action of amnioiiiacal silver oxide on (FENTON), T., 1297 ; Y., 1900, 148.Glyoxaline-red, formation of (RUHE- MANX and STAPLETOX), T., 809; eraminee, presence of invertase in some plants of the (O’SULLIVAK), T., 691 ; P., 1900, 61. Guaiacol, condensation of, wi tli e thy1 phenylpropiolate (RUHEMASS and 168. Guanidine, condensation of, with the ethyl esters of acetylenedicarboxylic and chlorofumaric acids ( RUHE- MAKN and STAPLETON), T., 805; P., 1900, 122. action of, on ethyl phenylpropiolate (RUHEMAKK and STAPLE~ON), T., 242 ; P., 1900, 12. 416 ; P., 1900, 44. P., 1900, 122. STAPLETON), T., 1180; P., 1900, H. Haematoporphyrin, actioii of bromine on (MARCHLEWSKI and SCIIUXCK), T., 1091 ; P., 1900, 149. Hematoxylin (GILBODY and P’BHKIS), constitution of (PEeK1,I- and YATES), Hn.niatoxyZo?L cccmpechia?turn, constitu- ents of (PEKKIN), T., 426 ; P., 1900, 45.Halogens, specific gravity of the, a t their boiling points (DKUGMAK and lLi,\rsaY), T., 1838 ; P., 1900, 172. P., 1899, 241. P., 1900, 108. Eeptanedicarboxylic acide. See : - Heptoic acid (a-isopropylbutyric ncitl, cth?ilisop?.opyZncetic acid) and its derivatives, preparation of (CROSSLNY 225. its ethyl ester, amide, anilide, and toluidide (CKOSYLEY and LS SuEuu), T., 93 ; P., 1899, 225. a-bronio-, ethyl ester, actioii of clietliylaniline on (CROSSLEY and LE SUEUR), T., 95 ; P., 1899, 225. Heptoic acid (aSB-triinetkyZb~6tl/1.ic acid) Y-cyano-, ethyl ester (THOIWE and YOUKG), T., 939 ; P., 1900, 115. Hexahydro-xylic acid. See Dimethyl- cyclohexanecarboxylic acid.Hexamethylene. See cycloHexaiie. Hexane (diisopropyl), preparation, vapour pressures, specific volumes, and critical constants of (Yorsc: and FORTEY), T., 1126 ; P., 1900, 165. cycZoHexane (hexnmcthy Zem), spectrum of (HARTLEY and DOBBIE), T., 846 ; P., 1900, 129. and mono- and di-chloro-, refraction and magnetic rotation of (YOUXG and FORTEY), T., 372 ; P., 1900, 44. Methylisopropylglutaric acids. Tetramethylglutaric acids. and LE SUEUK), T., 89 ; P., 1899, Hexanedicarboxylic aoide. See :- Dime t hyle t h y lsuccinic acid. 8- isoPropylglu taric acid. Trimethylglutaric acid. Hexanetricarboxylic acid. See Dinietliyl- butaiietricarboxylic acid. sgcZoHexene (telrnlzydrobe?~~nc), spec- trum of (HARTLEY and DOBUIE), T., 846 ; P., 1900, 129. Bexenoic acid (B-isopropylacrglic acid), ethyl ester, condensation of, with ethyl sodiocyanoacctate (HOWLES, TIIORPE, and UDALL), T., 943; P., 1900, 115.Homocamphanic acid, formation of (LAPWOKTH), T., 1066 ; P., 1900,128. z-Homocamphoramio acid, forination of (LAPWORTH), T., 1061 ; P., 1900, 128. Komocamphoric acid and its bromiiia- 1900, 128. a-bromo-, and its diethyl ester, action of bases on (LAPwOirrH), T., 1066 ; P., 1900, 129. Jomocamphoric dianilide ( LAPWOHTH), Xomocamphoronic acid (LAPWOI~TH and bromination of (LAPWORTH a i d CHAPMAN), T., 452 ; P., 1900, 56. ti011 (LAPWOlLTII), 1’. , 1053 j P., T . , 1063. CHAPMAN), l’., 309 ; P., 1900, 4.INDEX OF Hydrazine, clcctrolysis of (SZARVASY), T., 605 ; P., 1900, 3. Hydrazinosalicylic acid (ACDEN), P., 1899, 231. Hydrazoic acid.See Azoiniide. Hydrazone-compounds differentiated from azo-compounds by bromine (ARMSTROSG), P., 1899, 243. Hydrindamine chloro- and bromo- camphorsulphonates and c i s - s - camphanates, isomeric (KIPPISG), T., Hydrobromic acid (hylrogcn bromitle), preparation of p r e (Scorr), T., 648 ; P., 1900, 69. Hydrocyanic acid (hgrldroyciL cycmide), preparation of (BKOWNISG), T., 1235 ; P., 1900, 172. coiistitntion of (WADE), P., 1900, 156. dissociation constant of (WALKEI:. and CORJIACK), T., 15 ; P., 1899, 208. Hydroferrocyanic acid, constitution of', decomposition of, in air, actioii of heat and of ether on (B~LOIVSIXG), T., 1233; P., 1900, 172. decomposition of (ADIE and BROWS- IXG), T., 157 ; P., 1899, 226. Hydrogen bromide. See Hydrobromic acid. cyanide.See Hydrocyanic acid. nitride. See Azoiniide. 861 ; r., 1900, 51. Hydrogen peroxide, equilibrium between l'ersulphuric acid and ( LOWRY and WEST), T., 955 ; P., 1900, 1?7. action of, on carbohydrates, 111 pre- sence of ferrous salts (I\foRi:ELL 171. interaction of, with sulphnric acid (LOWRY and WEST), T., 950; P., 1900, 126. Hydrogen tetroxide, Bach's ( h A 1 - Hydrogen sulphide, dissociatioii coii- stant of (WALKER and CORJIACK), T., 14 ; P., 1899, 208. estimation of (RUSSELL), T., 354 ; P., 1900, 41. Hydroxyamidosulphatea, decoiiiposition of, by copper sulphate (DIVEKS and HAGA), T., 978; P., 1900, 147. o-Hydroxybenzoic acid. See Salicylic acid. Hydroxybenzylidene-2-naphthylamine, l-bromo- and l-chloro-o- and -p, and their hydrocyanides (MORGAN), T., 1216 ; P., 1900, 171. a-Eydroxycamphopyric acid (GARD= a-Hydroxyhomocamphoric acid, laotone CKOFI'S), 'r., 1219 ; P., 1900, STROSG), P., 1900, 134.XER), P., 1900, 46. of. See Homocamphanic acid. SUBJECTS. 1353 Hydroxylamine, spectrum of (HAKI'LEY and DOBBIE), T., 321 ; P., 1900,14. electrolysis of (SZARVASY), T., 608 ; P., 1900, 3. action of, on ethyl plieiiylpropiolate (RUHEMASX and STAPLETUS), T., 240 ; P., 1900, 11. hydrochloride,. gradual decomposition of, when impure (DIVERS and HAGA), T., 978 ; P., 1900, 147. 1 -Hy drox y laminocamphane (B- boriLy1- 1'. , 1900, 14. Hydroxymethylquinoxaline (RuILE- MASS and STAPLETUX), T., 249 ; P., 1900, 12. 2-Hydroxyisonicotinic acid, 6-chloro-, aiid &amino- (SELL a i d DoowoN), 'l'. , 236 ; P., 1900, 9. o-Hydroxyphenoxyacetic acid.See Catecholacetic acid. /ri-Hydrox y phenox yace tic acid ( tcso 1'- ~ ~ ~ L O Z C L C C ~ ~ C acid), and its silver salt and aiiilidc (CARIXR and LAWILESCE), T., 1222 ; l'., 1900, 152. p-Hydroxyphenoxyacetic acid ( p i 7 d - ncclic m i d ) and its aniline salt and anilide (CAxmit and L.IWHENCE), T., 1222 ; P., 1900, 152. a-Hydroxypropionic acid. See Lactic acid. 2-Hydroxypyridine, 3:4.5:6-tetmchloro- (SELL and D o o ~ w s ) , T., 772. Hydroxypyrimidinecarboxylic acid, amino-, ethyl ester of (RUHENANN awl SI'APLETOA), T., 808 ; P., 1900, 122. Hypobromous acid, action of, on aiiilides (CiIa.rr.-rwAY ancl OIXON), T., 789, 797; P., 1900, 102, 112; (AKMWROXG), T . , 1047 ; P., 1900, 160. action of, 011 tliacetyl-?,t-plienylene- dimiine (MOI:GAX), T., 1203 ; l'., 1900, 170.Hypochlorous acid, actioii of, og nnilides ( C H A ~ ~ . \ W A Y and O i : . r u s ) , T., 131, 789, 797 ; P., 1899, 232; P., 1900, 102, 112; (ClIATrAWAY, OmoN, ancl HURTLEI.), T . , 800 ; P., 1900, 125 ; (ARYSTI{OSG), T., 1047 ; P., 1900, 160. action of, on diacetyl- and dibenzoyl- nt-phenylenediamine ( MOILGAS), T., 1203 ; l',, 1900, 170. ~~,lJdl.OX!J~Ct?~Li?lC) (FORSTEI:), T., 255 ; I. Imidoaulphites (DIVEI.S and OGAWA), P., 1900, 113. 4 2 21354 INDEX OF SUBJECTS. Indene, new syntheses of (KIPPISG an( HALL), T., 467 ; P., 19q0, 54. Induline dyes, electrolytic preptiratio1 of (SZARVASY), T., 207 ; P., 1899 194. Invertase, presence of, in some plant! of the Gramineze (~'SULLIVAN), T. 691 ; P., 1900, 61. Iodates and hypoiodites, cstiinatioii o (0~1'0s and BLACKM.~~), T., 830 I'., 1900, 103.Iodine atom, confignration of the KIP^> ING arid PETERS), P., 1900, 62. action of, on alkalis (TAYLOIL), T., 725 ; P., 1900, 70. 1Jehaviour of, with mercuric oxide (ORTOS and BLACKMAN), T., 835 ; P., 1900, 104. Iodine monochloridc, reaction of, n ith alkalis (ORTON and BLACKMAN), T., 830 ; P., 1900, 103. J. Jaborandi leaves, alkaloids of (JOW ~ m ) , Jaborine (JOWETT), T., 473 ; P., 1900, 50. Japaconine, preparation, composition, properties and salts of (DUNSTAN and READ), T., 58; P., 1899, 207. Japaconitine, extraction, coniposition, properties, hydrolysis, salts, and physiological action of ( DUNSTAN and READ), T., 47 ; P., 1899, 206. Japbenzaconine, ireparation, propertics, hydrolysis and salts of (DUESTAX and READ), T., 65; P., 1899, 207.T., 478 ; P., 1900, 49. L. Lactic acid (i-etibylidenclnctic acid, a- hydroxypropionic wid), oxidation of, in presence of ferrous salts (FENTON and JONES), T., 71; P., 1899, 224. Lactone, C10H1602, from the bromination of homocamphoric acid (LAPWORTH), T., 1063 ; P., 1900, 128. Laevulomannan from Phytelephns macro- ccwpa, and its dibenzoyl derivativc (BAKER and POPE), T., 696; P., 1900, 72. isoLauronolic acid (LEES and PERKIX), and its stercoisomeride, reactions and structure of (WALKER and Coa- MACK), T., 374 ; l?., 1900, 58. Lead chlorate, decomposition of (SODEAU), Liquefaction of a ga.; hy " self-cooling" P., 1900,18. T., 717 ; P., 1900, 88. (NEWTH), P., 1900, 87. Luteolin, constitution and cliniethyl ether of (PERKIN), P., 1899, 242.and its methyl ethers, decomposition products and salts of (PERKIN and HORSPALL), T., 1314; P., 1900, 181. M. Magnesium potassium and magnesium rnbidium snlphates (MALLET), T., 219, 223 ; P., 1899, 227. Magnetic rotation. See Photochemistry. Malic acid, oxidation of, in presence 0 1 ferrous salts (FENTON and JONES), T., 75 ; P., 1899, 224. Malonamide, action of nitrosyl chloride on, and of hydroxylamine on its ciibromo-derivative ( WIIITELEY), T., 1040 ; P., 1900, 145. Malonic acid, ethyl ester, condensatioii of, with formaldehyde (BOTTOM- LEY and PERKIN), T., 294 ; P., coiidensation of the sodium deriva- tive of, with ethyl aa'-dibromo- BB-dirnethylglutarate ( PERKIN, THORIJE, and WALKER), P., 1900, 149. action of dry silver oxide and ethyl iodide on (LANDER), T., 743 ; P., 1900, 6, 90.Manganese potassium sulphate (h'iALLET), T., 221 ; P., 1899, 227. Mannogalactan from Strychnospolatorim and its dibenzoyl derivative (BAKER and POPE), T., 696; P., 1900, 72. Manures estimation of potash in (ADIE and WOOD), T., 1079 ; P., 1900, 17. Memorial lectures : Victor Meyer (THORPE), T., 169 ; P., 1900, 33 ; Bunsen (ROSCOE), T., 513 ; P., 1900, 84 ; Friedel (CILAFTS), T., 993 ; Nil- son (PETTERSSON), T., 1277. !-Menthol, action of dry silver oxide and ethyl iodide on (LANDER), T., 731 ; P., 1900, 6. Mercury, vapour deiisity of (BAKER), T., 648 ; P., 1900, 68. Mercuric iodide, action of, on alkyl sulphides (SMILES), T., 163; P., 1899, 240. oxide, action of iodine on (ORTON and BLACKMAN), T., 835 ; P., 1900, 104. lderouroua chloride, vapour density of dried (BAKER), T., 646 ; P., 1900, 68.iodide (RAY), P,, 1899, 239. nitrite, action of, 011 ethyl iodide (HAY), l',, 1899, 239. 1900,16.INDEX OF SUBJECTS. 1355 Heeitylene (1 :3 : 5 - t r i ? ~ e t l ~ y Z b e n ~ ~ ~ ~ ~ ) , re- fraction and magnetic rotation of (PERKIN), T., 267; P., 1899, 237. Mesityl oxide ( m t h g l isobziiexgl ketoize ; iso;uropylicEesieacetone), condensation of, with ethyl sodiometli~lmnIoiiate (CROSSLEY), P., 1900, 90. Mesoxamide, oxiine of, and its salts ant1 ncetyl and ethyl derivatives, and thc action of nitrous acid on (WIII ~EIXY), T., 1040 ; P., 1900, 145. Metahemipinic acid (GII~BO~Y and PERKIS, and YATES ; J’ERRIS and YATEY), P., 1900, 107. Mqrtal-ammonia compounds, natnro of, in aqueous solution ( DAWSOS and ~IIcCEAE), T., 1239; P., 1900, l i 2 .Methane, nitro-, action of alkalis and ainnionia on (DUNSTAS and Gor.1,~- ISG), l’., 1262 ; P., 1900, 1’74. Methazonic acid, preparation, constitrr- tioii and reactions of (DEWTAX and GOULDIKG), T., 1264; P., 1900, 174. p-Methoxybenzylidene-2-naphthylamine, l-bromo- and l-chloro-, ancl their hydrocyanides (MORGAX), T., 1216 P -0- Met hox yphenoxy cinnamic acid and its ethyl ester (RvnExrass and STAPLE~OS), T., 1180; P.. 1900, 168. o-Methoxyphenoxystyrene (RUIIEMAYN and STAPLETON), T., 1181; P., 1900, 168. Methylacrylic aoids, a- and 8-, ethyl esters, condensation of, with etllyl sodiocyanoace tatc (110 WLES, Tito ILIT, UDALI,, and NEALE), T., 0 4 i ; P., 1900, 116. Methylamine, spectrum of ( HARTLEY and DOEBIE), T., 320 : P., 1900, 14.action of iodine chloride on (0 I:TOS and BLACKJIAS), T., 833 ; p., 1900, 103. aal-Methylisoamylsuccinic acid and its oxidation products (Lawmwc), 1’. , 1900, 156. aal-Methylisoamylsuccinic acids, cis- antl trrins-, dissociation constants of (130s~ and ~ITASKLISG), T., 1301 ; I’., 1900, 154. Methyl isobutenyl ketone. See X c s i t j l oxide. a-Me thyl- a,:isobu tylglu taric acid, a i d its oxidation, and al-cyano-deiivative (TAWRESCE), 1’. , 1900, 155. Methylisobutylglutaric acids, cis- ant1 trans-, and their anhydrides and niiilic acids (LATVRRSCE), P,, 1900, 13-k. a-Me thyl-al-isobutylpropanetricarboxyl- ic acid, and its ethyl ester (LAJY- I~ESCE), P., 1900, 154. 1’ERI<IS), P., 1899, 241 ; (GILEO~Y, l’., 1900, 171, aa,-Methylisobutylsuccinic acids,cis- and tmizs-, preparation antl dissociation constants of (BOSE and SPFLISKLISG), T., 1303 ; P., 1900, 184.Methylbutyric acid. See Valcric acid. Methylcarboxyresorcylac~tic acid (GIL- 106. Methylcyanoacetic acid, ethyl ester, constitution of the kodinm derivative Methyldiethylsulphine iodide mercnric iodide (SJrILES), T., 162; P., 1899, 240. Methylenebis- 1 -bromo- and - l-chloro-2- naphthylamine (MORGAK), T., 814 ; l’., 1900, 131. pit- and 13 Methylenemalonic acids, ethyl esters, preparation ancl distillation of (BonoMLET and PERKIS), T., 306 ; 1’. , 1900, 16. Methylenemalonic and $1-Methylene- malonic acids, ethyl esters, hydrolysis of ( R O ~ ~ T O ~ , E Y a i d PERI~IS), T., 306 ; P., 1900, 16. Methyl ethyl sulphicle-mercuric iodide (SMILES), T., 164 ; P., 1899, 240.Methylethyldesylsulphine bromide ancl picrate (SMILES), T., 1175 ; P., 1900, 168. rl- and I-Methylethylphenacylsulphine tl-bromocamphorsnlphonates and picrates (SIIILES), T., 1175 ; I?., 1900, 168. i-Methyle thylphenacylsulphine bromide and picrate (SMILES), T., 1175 ; I’., 1900, 168. tZ-Methyle thyl-11-propyl tin iodide (POPE and PEACIIEY), I?., 1900, 42. d- bromocamphorsulphoilate ( Pom and PE.UXET), P., 1900, 116. Methylethylthetine, attempts to resolve (SJIILES), T., 168 ; P., 1899, 240. resolution of, into activc components (POPE and PI:ACHEP), T., 1072; P., d-Methylethylthetine platinichloride, d-camphorsulphonatc, and d-bromo- cainpliorsulplionate (POPE aiitl Methylglutaric acids, a- and B- (bzcfmc- t l i c c t , ~ ! ~ ~ y I i c ncitls) (~IOJVLES, THORI’E, and UDAT.~.), T., 947 ; P., 1900, 116.Me thylglyoxal-p- ethoxyphenyl- hydraz- oxime, -0sazone and -0sotetrazone ( A i . n ~ s ) , l’., 1899, ’230. Kethylglyoxal-methylphenylphenyl- osazone and -salicylic acid osazone (ATTEA-), P., 1899, 231. Kethyuapaconitine and its anrichloride (DUNSTAN and READ), T., 54 ; P., 1899, 207. CODY, l’EKKIS, alld Y-\’rlC>), P., 1900, of (THORPE), T., 923 ; P., 1900, 113. 1900, 12. PEACIIEP): rr., i o n ; P., 1900, 12.1356 INDEX OF SUBJECTS. lethylmalonic acid (isosuccinic acid ; ethanedicarbox y Zic mid), sodium deriva- tive of the ethyl ester, condensation of, with mesityl oxide (CI:OSSLET), P., Methylisopilocarpine and its salts (JOWETT), T., 8 5 3 ; P., 1900, 125. Cymene. a-Methyl-8-isopropylglutaric acids ( hepf nncclicnrboxy 1 ic ncids) ( H o WLES, THORPE, and UDALL), T., 946; l’., 1900, 115.aal-Methylpropylsuccinic acids, cis- and tmns-, preparation and dissocia- tion constants of (BOXE and SPRAKK- LING), T., 1302; P., 1900, 184. Methylresorcinolacetic acid (GILBODY, PERKIN, a:id YATE~), P., 1900, 106. Mixtures, refraction of (Pmi;rx), T., 280 ; P., 1899, 237. Morphide, chloro-, and bromo-, and their hydrochlorides and liydrobroinides (SCHEPVER and LEES), T., 1024 ; P., 1900, 143. isoMorphine and its hydrochloride, hydro- bromide and nietliiodide (SCl1RYvEI: and LEES), T., 1024 ; P., 1900, 143. methiodide, action of silver sulphate and barium hydroxideon ( SCIIRTVER and LEES), T., 1024 ; P., 1900, 143. Mncic acid, oxidation of, in presence of ferrous salts (FENTON and JOSES), T., 76 ; P., 1899, 224.@jTicn Gale, constituents of (PERKIN), T., 429 ; P., 1900, 45. Myricetin from various tannin matters (PERKIN), T., 423 ; I?., 1900, 45. 1900, 90. 1:4-lKe thylisopropylbenzene. See N. Naphthalene, vapour pressure of (ALLEN), T., 400 ; P., 1899, 122. 8 - Nsphthalenecarboxy lic acid, e thy1 ester, chloroimide of (STIEGLIW and &Naphthol derivatives, ctherification of (DAVIS), T., 3 3 ; P., 1899, 210. Naphthols, a- and P-, condensation of, with ethyl phenylprolJiolate (BUTIE- MANS and BEDDOW), T., 9s-1 ; P., 1900, 123. 8-Naphthoxycinnamic acids, a- and B- (RUIIEMAKX and ]3Enno\V), T., 984 ; 8-Naphthyl methyl, ethyl, and propyl ethers and their halogen derivatives (DAYIS), T., 36 ; P., 1899, 210. SLOSSON), P., 1900, 2.l’., 1900, 123. B-Naphthylamine derivatives, action of aromatic aldehydes on (MORGAN), T., 1210 ; P., 1900, 171. Naphthylamines, action of formaldehyde on (MORGAR), T., 814; P., 1900, 131. Nascent state, influence of, on the cornhination of oxygen and carbon monoxide (RUSSELL), T., 361 ; I’., 1900, 42. Neobornylamine, separation of, from hornylamine, rotatory power of, and action of ethyl oxalate on (FORSTEP. and HART-SMITH), T. , 1152 ; P., 1900, 166. Nickel sulphate, combination of, with ammonia in aqueous solution (DAw- SOX and I\~cCR.ZE), T., 1247 ; P., 1900, 173. potassium sulphate (HALLET), T., 221 ; P., 1899, 227. isoNicotinic acid (4-~z~l’idil~ecnr602z~lic mid), 2:G-diiodo- (SELL and D0o.r- sos), T., 235 ; l’., 1900, 9. Nitrification, recent researches on (WAI~ISGTOS), P., 1900, 65.Nitritohydroximidosulphates (DII-ERS and HAGA), T., 432 ; P., 1900, 54. Nitrogen, atomic weight of (DEAK), T., 117 ; P., 1899, 213. quinquevaleiit, isomeric partially racemic salts containing (KIPPINO), T., 861 ; P., 1900, 51. specific gravity of, a t its boiling point (DRUGMAX and RAMSAY), T., 1228 ; Nitrogen bromides and chlorides, sub- stituted (ARMSTROSG), T., 1047 ; 1’. ,1900,160 ; (STIEGLITZ and Srm- SON), I?., 1900, 2; discussion, l’., 2. method of transforming ( CHATT- AWAY and ORTOS), T., 796. from 0- and pacetotoluidides (CIIATTAWAY and OETOS), T., 789 ; I?., 1900, 102. ortho-substituted, and their trans- formation (CHATTAWAY and ORTON), T., 797 ; P., 1900, 112. Nitrogen chlorides, substitnted (CHATT- AIVAY and OILTOS), T., 134 ; P., 1899, 232.from 5,1-chloroacetanilide (CIIATT- A W ~ Y , OI:TOS, and HURTLEY), ‘l’., 800 ; P., 1900, 125. Nitrous acid, sulphonation of, by sulph- urous acid (DIVERS and HAGA), T., 688 ; I?., 1900, 70. Nitrites, interaction between snlphites an(l (DI\-Ei:s and HAG.\), T., 673 ; Nitro-group, elimination of a, during tliazotisatioii ( MELDOTA and WECHS- LICI:), ‘l’., l l i 2 ; l’., 1900, 167. P., 1900, 172. I’., 1900, 70.INDEX OF SURJECTS. 1357 0. Obituary notices :- Peter Waage, T., 591. William Harkness, T., 592. J. F. Hodges, T., 593. William hiarcet, T., 594. George Henry Ogston, T., 594. ltobert Oxland, T., 595. llichard ‘l’ayler Plimpton, T., 595. Henry Charles Repoltls, T., 596. Edward C. Cortis Stanford, T., 597. Sidney Augustus Sworn, T., 598.Willhm Thorp, T., 599. Johnnn I<. F. Ferdinand Tieniann, T., David Watson, T., 603. n-Octane, vapour pressnres, specific volumes, arid critical constants of (J’ouKG), T., 1145 ; P., 1900, 166. Octane (ciiisobzLtyZ), preparation, vapoiir pressures, specific volumes, and critical constants of (YOUKG and FOWEY), l’., 1126 ; P., 1900, 165. Octanedicarboxylic acids. See :- Dipropylsuccinic acids. I’ropylisopropylsuccinic acids. Oleic acid, action of dilnte nitric acid 011 (EDMED), P., 1899, 190. Orcinoltricarboxylic acid, methyl and ethyl esters, formation, constitution and nitrationof (Doo~sos), T., 1195 ; nitro-, hydrolysis of the methyl ester, and reduction of the methyl and ethyl esters of (DOOTSON), T., 1199 ; P., 1900, 170. Orientation, influence of various groups Osones, formation and isolation of (MORRELL and CiioFrs), T., 1219; P., 1900, 171.Oxalacetic acid, preparation, properties and reactions of (FENTOS and JOXES), T., i 7 ; l’., 1899, 224. Oxalic acid, formation of, from dehydro- lioniocamphoric acid (LAPWOIWH), T., 1070, ethyl ester, condensation of, with ethyl crotonate (LAPWORTH), P., 1900, 132. y-Oxalocrotonic acid, ethyl ester (LAP- isoOxazoles, formation of ( D r s s ~ a s and GOULDISG), T., 1266 ; P., 1900, l i 4 . Oximinopropionic acid, hydroxamic acid of (WHITELRP), T., 1040 ; p., 1900, 145. Oxyazo-compounds, broniinatiou of 600. P., 1900, 170. 011 (LAPWOKTII), P., 1900, 108. WORYH). P., 1900, 132. (ARMSTROA-G and IRHEl?\VOOl)), P., 1900,158. o-Oxycarbanil and its ethers, absorption spectra of (HARTLEY, DORBIE, and P.kLIATSEAS), T., 839 ; P., 1900, 1 :30.Oxygen, evolution of, from chlorates (SODE.W), T., 137, 717; Y., 1899, 157; 1900, 88. specific gravity of, a t its boiling point (DHUGMAN and RAMSAY), T., 1228 ; P., 1900, 172. influence of the nascent state on the combination of carbon monoxide alld (Rcs-ELL), T., 361; P., 1900, 42. combination of, with sulphnr dioxide (RUSSELL and SMITH), q’., 340 ; P., 1900, 41. P. Paraffins, nitro-, action of alkalis on, and rcdnction of, and of their salts (DUSSTAS and GOULDISG), T., 1266 ; l’., 1900, 1’75. Pentamethylene (cyclopentnne) deriva- tives, new series of (PERKIN, THOEPE, and \VALKEK), P., 1900, 149. Pentamethylenehexacarboxylic acid (BwrTomEY and ~’EI:I;Ix), T., 294 ; P., 1900, 16. Pentamethylene- 1:2:4- tricarboxylic acids, cis- and trans-, synthesis of (Bo,rrow.m and PERKIN), T., 296 ; P., 1900, 16.Pentanehexacarboxylic acid, ethyl ester ( B o r m m E Y and I’EKKIN), T., 294 ; P., 1900, 16. Pentanetricarboxylic acid and its decomposition (Bori OXLEY and Phenacetyltartaric acid, diethyl ester, rotation of (MCCRAE and PATTERSON), T., 1096 ; P., 1900, 161. Phenol, dissociation constant Of (WALKER and CORMACK), T., 18 ; I’., 1899, 208. condensation of, with ethyl phenyl- propiolate (XUHEMASS and BED- DOW), T., 984; P., 1900, 123. Phenols, action of, on ethyl acetylenedi- carboxylate (RUHE~IANS arid BED- IJOW), ‘l’., 1119 ; P., 1900, 165. action of, on ethyl pheiiylpropiolate (REHEMASS and BEDDOW), T., 954, 1119 ; P., 1900, 123, 165. Phenolazobenzeneazophenol and its diacetyl derivative ( MELDOLA arid WILLIAMS), P., 1899, 196.B-Phenoxycinnamic acid and its ethyl ester (EUHEhlANS and BEDDOW), T., ~ ’ E I ~ K I S ) , rr., 294 ; P., 1900, 16. thio-. See Phenyl niercaptan. 954 ; I]., 1900, 123.13523 INDEX OF SUBJECTS. 8.Phenoxycinnamic acid, ethyl ester? action of snlphuric acid on (1tumMtlm a11d STAPLETOK), T., 1183; P., 1900, 168. Phenoxyfumario acid and its ethyl ester and aniide (RUHEMANN a d BEDDOW), T., 1119; P., 1900, 165. actionof sulphuric acid on (RUHEMAXX and STAPLETON), T., 1180 ; l'., 1900, 168. Phenoxymaleic acid (RUHEMASK and BEDDOW), T., 1119 ; P., 1900, 165. Phenoxystyrene (RUHEMASS and BED- now), T., 984; P., 1900, 123. Phenyl acetyl nitrogen chlorides, chloro-derivatives of (acetyllchdoro- nininochlorobcn~enes) (CITA'I"I.AIV'AT, ORTON, and HUIITLEY), T., 800 ; P., 1900, 125.Phenyl acetyl nitrogen chlorides and bromides (neetyl-ch lwo- and -bronz o- antinobciiwtes) and their transform- ation (CHATTAWAY and Omox), T., 798 ; P., 1900, 112. Phenyl acyl nitro en chlorides, p-nioiio- anci 2:4:6-tTi-cfloro- (CHATTA\~~AP and Omos), T., 134 ; P., 1899, 232. Phenyl acyl nitrogen chlorides and bromides, and their behavionr to alkalis, potassium cyanide, and zinc ethyl (STIEGLITZ and SLOSSOS), 1'. , 1900, 1 ; discussion, P., 2. Phenylacetylchloramine, discrepancies in the description of its properties, and explaiiation of the riianner i t undeygoes isomeric change (ARM- GTROSG), T., 1047; €'., 1900, 160, 8-Phenylcinnamic acid, thio-, and its ethyl eater (RUHEMAPTN and STAPLE- TON), T., 1181 ; P., 1900, 168.2-Phenyl-4 5 -cis-diphenyl-4 5 - dihydro - imidazole. See Aniarine. 2-Phenyl-4: 6 -trrrns-diphenyl-4 5 4 - hydroimidazole, See isoAmarine. mPhenylenediacety1-dichloro- and -di- bromo-amine (MORGAN), T., 1203 ; P., 1900, 170. m-Phenylenediamie, acyl derivatives, action of hypochlorous and hypo- bromous acids on (MORGAN), T., 1203 ; P., 1900, 170. l-moxo- and1 :5-di-chloro- and -bromo-, and their dibenzoyl and diacetyl derivatives (MORGAN), T., 1202 ; P., 1900, 170. o-Phenylenedioxydiacetic acid and its ethyl ester, nietallic and aniline salts, amide, and anilide (CARTER and LAW- EENCE), T., 1222; P., 1900, 152. m-Phenylenedioxydiacetic acid and its ethyl ester, metallic and aniline salts, amiilc, and anilicle and 2:4:6-trinitro- derivii tive (CAIvrER and Ilaw ILEXTCE), T., 1222 ; P., 1900, 152.p-Phenylenedioxydiacetic acid and its ethyl ester, metallic salts and anilide P., 1900, 152. ( C h I x E R and LAWKESCE), T., 1222 ; Phenylethane, See Etliylbenzene. Phenylfumaric acid, tliio-, and its ethyl ester (RTJHEMAXN and STAPLETOS), T., 1183 ; P., 1900, 168. C- Phenylhy droxy tr iazole, and st-ni tro- and acetyl derivatives (YOUNG and WITHAM), T., 224 ; P., 1900, 5. Phenyl mercaptan, condensation of, with ethyl acetylenedicarboxylate and with ethyl phenylp~opiolate ( RUIIE- nrAxN and STA~'I~ETOK), T., 1181 ; P., 1900, 168. 5-Phenylisooxazolone (RUHEMANN and Phenylpropiolic acid, ethyl ester, action of benzamidine, of hyclroxylamine, of thiocarbamide and of gnanidinc 011 ( R r HENANN and STAPLETOS), T., 239 ; P., 1900, 11.condeiisation of, with guaiacol ant1 mitli plienyl mercaptan (Rcrm- 1181 ; P., 1900, 168. action of phenols on (RUHEMAKK Phenylstyrene, tliio- ( I~YIIEMAKN and STAI~IXIUX), T., 1182 ; P., 1900, 168. Phenyl-p-tolyliodonium hydroxide, iodide, and I~roniocanipl~oisul~,I~o~iate (KIPPIXG and PETEILS), P., 1900, 62. Phloroglucinol from the fusion with nl- kali of colouiing matters from tannins (PEM~Ix), T., 424 ; P., 1000, 45. Rotation of d- and Z-isoamatrine and their acid tartrates (SSAYE), T., iS4 ; P., 1900, 118. of bornylsmine salts, bornyloxam- ide, diborngloxamide, and neo- boriiylamine (For:sr~R and HAXT- S h f m r ) , T., 1162 ; l'., 1900, 166. of cainphoroxinieacctic acid and its s d t s (FomTEI: and HART-SMITH), of hydrindaniine bromo- and chloro- cainp1iorsnlI)honates and cis- r-camphanates (I<IrI'IsG), Y'., 884 ; P., 1900, 51. of n~ethyletliylplicnacyls~il~~hiiie cE-bromocainl,horsulphouates and picrates (SMILES), T., 1177 ; P., 1900, 16s. STAPLETON), T., 247 ; P., 1900, 12. MANX nlld STAPLETOS), T., nlld BEDDOW), T., 984, 1119; P., 1900, 123, 165. PHOTOCIIEMISl'ET :- T . , 1154 ; P., 1900, 166.INDEX OF SUB,JECTS. 1359 ~HOTOCHE~IISTRT :- Rotation of cl-iiietliylethyltlietine pla- tinichloride, d-campliorsulplion- ate, and rl-broniocamphorsulplii~ii- ate (POPE and PE,~CIIEY), T., 1072 ; P., 1900, 12. of ~-iiitrocaml,haiie (For:sTEr,), T., 258 ; P., 1900, 13. of pilocarpinc, isopilocarpine :Lnd pilocarlkliiie and their salts of‘ acetyl and phenacetyl derivatives of dietliyl tl-tartrate (BICCRAE and I’z\rrmriso~), T., 1096 ; P., 1900, 161.Magnetic rotation of the 1)enzenoid hydrocarbons ( PEI:I;JS), 1’. , 267 ; P., 1899, 237. of liesametliylc~ic and wzono- and cli- cliloroliexniiietliyle~~e (PRRJ;IN), T., 372 ; I)., 1900, 44. Refraction of mistnres (PERKIN), T., 280 ; P., 1899, 237. of the henzenoid hydrocarbons ( ~ ’ ~ ~ I ~ I ~ I K ) , T., 267 ; l’., 1899, 237. of hexamethylene and wzono. and rli-chloroliexaniethylcne( PEI:KI s), T., 3i2 ; l’., 1900, 44. Spectrographic method, value of, in tautoinelism (I-Iarirr,s~ and Doe- BIE), T., 498 ; P., 1900, 57. Spectra of ammonia, metliylaniine, hydroxylaniiiic, acetsldoxinie ancl acetoxime (HAIWLIW and Dor3- of benz-anti- and -syii-aldoximes (HAJ:TI,EY and D o n e i ~ ) , T., 509 ; P., 1900, 58.of 2:5dirnethylpyrazine (HAr,TLET and DOBBIE), T . , 846 ; P., 1900, 129. of ethyl d ibenzoylsuccina t c s (IIARTI,EY slid DOBBIE), T., 498 ; ME), rr., 318 ; P., 1900, 14. P., 1900, 57. of liexamethylene aiid tetraliydro- lmizene (HAIW,EY and DOBME), T., 546 ; l’., 1900, 129. of o-oxycarbanil and its ethcrs (I I A KT LEY, Do B I< I s, and PA LI AT - of chloropliyll and its colouring ancl SEAS), rr., 8x1 ; P., 1900, 130. ScrrYxcr;), l., lOS0 ; P., 1900, in a t t c rs 148. of broinoli~matoporl,liyriii and bromopliSlloport)liyl.in ( RIn~cir- I,EWSICI and Scrrvscr;), T., 1093. Spectrometer scale reader, improved Phylloporphyrin, action of broniine on (?!A I:C I I I, EIVS I; I ( P E n I i r s ) , T., 201. (h1AI:CHLE\VSI<I aiid SCHYSCK), T., 1091 ; P., 1900, 149.Physiological action of japacoiiitine (DUSSTAN and READ), T., 53. of pilocarpine, isopilocarpine, and pilocarpicliiie (JowETr), T., 497. Picric acid (2: 4: G-triliit rophenol), oxida- tion of, in presence of ferrous salts (Fes~ox aiicl JOSES), T., 76; Pa, 1899, 22-1. Pilocarpidine, constitution, properties 2 n d salts of (JOWETT), T., 473; I?., 1900, 50. Pilocarpine and isopilocarpine, con- stitution, properties, reactions, salts aiid physiological action of (JowET’I‘), T., 473 ; P., 1900, 49. Pilocarpine, constitution of (JOWET r), T., 494, 851 ; P., 1900, 50, 123. icoPilocarpine, oxidation of, with permxnganate, and reactions of, with soda lime, fwed canstic potash, and methyl iodide (JOWETT), T., 551 ; P., 1900, 123. Piluvic acid, C8Hl4O6 (JOWETT), T., 855.Potassium carbonate, solubility of solotions of, in aqueous ammonia (NEWTII), T., 775 ; P., 1900, 87. clilorate, decomposition products of (SO~EAU), T., 142 ; P., 1899, 157. nitrite, decomposition of, by alcoholic sulphur dioxiile (DIVERS and HAG’\), T., 437, 687. and nitrate, mixed, solubility of ( D I Y I ~ s ) , P., 1900, 40. Dipotassium sodium cobaltinitritc (ADIE and WOOI)), T., 1076 ; F., Potassium sulphates, compounds of, with inetallic sulpliates ( K m x r ) , T., 216 ; P., 1899, 227. nitritoliydrosimidosulpliates (DIVERS aiid HAGA), T., 432 : P., 1900, 54. snlpliazotised salts, Freniy’s, identifica- tion and constitution of (DIVERS liydrosulpliides, snlphicles, and poly- sulphidcs (I~LOSAJI), T., 753 ; p., 1899, 146. Potassium organic compounds :- fcrrocyaiiide, clecompositioii of, by sulphuric acid ( ADIE and BROWS- IKG), T., 150 ; P., 1899, 226.Potassium, new method of cstiniatiirg (ADIE and WOOD), T., 1076 ; I’., Propane, nitro-, secondary, action of alkalis on ( D u s s ~ ~ w aiid GOI~I~IILNG), T., 1266 ; P., 1900, 174, Propanedicarboxylic acid. See Glutaric acid. cgcZoPropanedicarboxylic acid. See Trimetliylenedicarboxylic acid. 1900, 17. nncl HAGA), rr., 440 ; P., 1900, 55. 1900, 17.1360 INDEX OF SUBJECTS. n-Propyl isocyanide (WADE), P., 1900 157. B-isoPropylacrylic acid, See Hexenoic acid. Propylbenzenes, n- and iso-, refractioi and magnetic rotation of (PERIIIN)! T., 267 ; P., 1899, 237. a-isoPropylbutyric acid. See Heptoic acid. 15-isoPropylglntaric acid (hexai~cdicarb. oxylic acid) (HOWLES, THORPE, and UDALL), T., 942 ; P., 1900, 115.isoPropylideneacetone. See Mesityl oxide. aa,-Propylisopropylsuccinic acids, cis- and trans- (octunedicarboxglic acids), preparation and properties of (BONE and SPBASKLING), T., 654 ; P., 1900, 71. Protocatechnic acid (3:4-dihgdrox?/- benzoic acid), from the fusion with alkalis of certain colouring matters from tannins ( ~ I S R K I S ) , T., 424 ; P., 1900, 45. Pyridine, chlorine derivatives of, con- stitution of (SELL and DOOTSOX), T., 1,233 ; P., 1899, 205 ; 1900, 9. chloroamino-derivatives of, constitu- tion of (SELL and DOOTSOK), T., 4, 233, 771 ; P., 1899, 206 ; 1900, 9 , 111. Pyridine-4-carboxylic acid. See iso- Nicotinic acid. Pyrojapaconine, reparation, properties and aurichloriA of (DUNSTAN and READ), T., 6 2 ; P., 1899, 207.Pyrojapaconitine ,preparation, properties, hydrolysis, and salts of ( DT;XSTAN and READ), T., 60 ; P., 1899, 207. Pyromncic acid, oxidation of, in presence of ferrous salts (FENTON and JONES), T., 7 6 ; P., 1899, 224. a-Pyrone-a‘-carboxylic acid (LAP- n-Pyrotartaric acid. See Glutaric acid. Pyruvamide, oxime of (WHITELEY), T., WORTH), P., 1900, 132. 1 0 4 5 ; P., 1900, 145. Q. Quercetin from various tannin matters (PERKIN), T., 4 2 3 ; P., 1900, 45. Quinolacetic acid. See p-Hyclroxy- phenoxyacetic acid. Quinoxalidoneacetic acid, ethyl ester (HZ;HEMANN and STAPLETOS), T., 243 ; P., 1900, 12. R. Racemisation occurring during the form- ation of henzylidene, benzoyl, and acetyl derivatives of d-ac-tetra- hydro-&naplithylamine (POPE and HARVEY), P., 1900, 74.of optically active tin compounds (POPE and PEACIIEY), P., 1900,116. Rain-water collected. a t Cirencester, amount of chlorine in (KIXCH), T., 1271 ; P., 1900, 183. Refraction. See Photochemistry. Resorcinolacetic acid. See m-Hy droxy- phenoxyacetic acid. Rhamnose, oxidation of, by hydrogen peroxide (Moncrc~r, and CROFTS), T., 1220 ; P., 1900, 171. Rhus Mctopizsnz, constituents of (PERKIN), T., 427 ; P., 1900, 45. Robixia Pssrcdncacia, constituents of (PERKIN), T., 4 3 0 ; P., 1900, 4 5 . Rubidium magnesium sulphate (MAT,- LET), T., 223 ; P., 1899, 227. S. Saccharic acid, oxidation of, in presencc of ferrous salts (FENTON and JOXES), T., 7 6 ; P., 1899, 224. Saccharose. See Sucrose. Salicylic acid, action of dry silver oxide and methyl iodide on (LASDER), T., 745 ; P., 1900, 6, 90.Salinigrin, new glucoside from willow bark (JOWETT), T., 707 ; P., 1900, 89. Saponification, the theory of (LEWIIO- WITSCH), P., 1899, 190. 3emicarbazone8, decomposition of (KtP- hydrolysis of (YOUNG and \vITHAM), 3ilico-phenylamide, diphenylimide, and -triphenylguanidine (REYNOLDS), T., 836 ; P., 1900, 133. Silver oxide, dry, and alkyl iodides, alkylation by means of (LANDER), T., 7 3 6 ; P., 1900, 6 , 90. iilver, estimation of, by Volhard’s method (ROSE), T., 232 ; P., 1900, 5 . iilver bullion, assay of (KOSE), ‘l’. , 232 ; iodium cobalt nitrite, and salt of, with yotassiuni (Anm and WOOJ)), T., 1076 ; P., 1900, 17. hydroximidosulphate, gradual de- composition of (DIVERS and HAGA), T., 978 ; P., 1900, 147. Iiydrosnlphides, sulphides and poIy- snlpliides (BLOXAM), T., 753 ; P., 1899, 146.PING), P., 1900, 6 3 . P., 1900, 7 3 . P., 1900, 5.INDEX OF SUBJECTS. I361 Sodium sulphite, decomposition of an ice-cold solution of, by carbon di- oxide (DIVERS and HAGA), T., 681. soils, estimation of potash in (ADIE and WOOD), T., 1079 ; P., 1900, 18. Solubility of potassinm carbonate solu- tion in aqueous ammonia, and r i c e z~ersd (NEWTH), T., 775 ; P., 1900, 87. of mixed potassium nitrite and nitrate (DIVERS), P., 1900, 40. Solutions, inorganic, partially miscible (NEWTH), T., 775 ; P., 1900, 87. Specific rotation. See Photochemistry. Spectrometer scale reader, improved Spectrum, See Photochemistry. 6‘-Styrenylhydroxytriazole and its acetyl derivatives (YOUNG and Substance, N,H,S,O,, and its salts, from the decomposition of ammonium aniidosulphite (DII’ERS), 1’., 1900, 104. C,H,Br,, from the action of bromine on caniphononic acid ( LAPWORrH and CloHl,06N,,. from a-dibromocamphor and riitrIc acid (LAPWORTH and C1;H,,O,, from the action of alcoholic potash on acid, ClgHlgOg (GILBODT, PRRIcIs, and YATES), I?., 1900, 107. C19H180,, from the action of phenyl- hydrazine on trimethylbrazilone (GILBODY, PERKIS, and YATES), P., 1900, 105. C,,H,,ON, from the action of formalde- hydc on ethyl-B-naphthylamine hydrochloride in alcoholic solution (MoRG.w), T., 819; P., 1900, 131. C,5H4202N2, from the action of benz- aldehyde on ethyl-B-naphthylamine (MOBGAS), T., 1210 ; P., 1900, 171. Substitution in phenols, inhibiting effect of etherification on (ARMSTROSG and LEWIS), P., 1900, 157.Succinic acid (~thaitedicccl.box~Zic ncid), dicyano-, ethyl ester (THORPE and YouSG), T., 937 ; P., 1900, 115. isoSuccinic acid. See Methylmalonic acid. Succinic acids, alkyl snbstituted, pre- paration and dissociation constants of (BOSE and SPRANKLIKG), T., 654, 1298; P., 1900, 71, 184. Sucrose (saccharosc, cane sqbgar), oxida- tion of, by hydrogen peroxide (MUI~I~ELI, and CROFTS), T., 1220 ; P., 1900, 1T1. (I’ERKIN), T., 291. ~VITIIAY), T., 230 ; P., 1900, 5. CIIAPMAK), T., 466; P., 1900, 57. CHAPMAN), T., 309 ; P., 1900, 4. Snlphazotised salt#, Fremy’s (DIVERS and HAGA), T., 440 ; P., 1900, 55. Sulphur, stereochemistry of (SMILES), T., 160, 1174; P., 1809, 240; 1900, 168; (POPE and PEACHEY), hydride. See Hydrogen sulphide.dioxide, combination of, with oxygen (RUSSELL and SMITH), T., 340 ; P., 1900, 41. action of dry ammonia on (DIVERS and OGAWA), T., 327; P., 1900, 38 ; (DIVERS), P., 1900, 104. estimation of (RUSSELL), T., 352 ; P., 1900, 41. Sulphuric acid, interaction of, with hydrogen peroxide (LOWRY and WEST), T., 950; P., 1900, 126. action of, on potassium ferrocyanide (ADIE and BROWNIXG), T., 150 ; P., 1899, 226. separation of, from vanadium (GOY- DEB), T., 1096. Sulphites and nitrites, interaction between (DIVERS and HAGA), T., 673 ; P., 1900, 70. Persulphuric acids ( LOWRY and WEST), T., 950; P., 1900, 126. Sulvanite from South Australia (GOY- DEK), T., 1094 ; P., 1900, 164. rr., 1072; P., 1900, 12. Sulphur acids :- T. Tannins of Arctosfaphylos Uva-ursi, Emntatoxylmt cawtpeckinia~cnz, Rhics i)letopizc?n, Af?friccc Gale, coriar ia Myrt~olicL, and Robinia Psezdacacia (PERKIK), T., 424 ; P., 1900, 45.d-Tartaric acid, diethyl ester, prepara- tion and rotation of acetyl and phenacetyl derivatives of (MCCRAE and PATTERSON), T., 1096; P., 1900, 161. Tartronic acid, oxidation of, in presence of ferrous salts (FENTON and JONES), T., 71 ; Y., 1899, 224. Tautomerism, spectrographic studies in ( HARTLEY and DOBBIE), T., 498 ; P., 1900, 57; (HARTLEY, DOBBIE, and PALIATSEAS), T., 839 ; P., 1900, 130. Temperature, See Thermochemistry. 2:2’-Tetrabenzyldiamino-l:l’-dinaphth- ylmethane (MORGAN), T., 814; P., 1900, 131. 2 2-Tetraethyldiamino- 1: l’dnaphthyl- methane (MORGAN), T., 814; P., 1900, 131. 1: 2:3:4Tetraethylbenzene, refraction and magnetic rotation of (PERKIN), T., 267 ; P., 1899, 237.1362 INDEX OF SUEJECTS.Tetrahydrobenzene. See cycloHexeiie. Te trah ydrof urfuran- 2 5 - dicarboxylic acid, its synthesis, hydrate and isom- eride (LEAN), T., 105 ; l’., 1899, 198. d-oc-Tetrahydro-B-naphthylamine, race- ivisntioii occurring during the forma- tion of benzylitlene, benzoyl, a n d ncetyl derivatives of (POPE aiicl HARVEY), l’., 1900, 74. Tetrahydroxyflavone. See Luteolin. Tetrahydro-xylic acid (T,EICS ancl YEBKIN), P., 1900, 20. 2:2’-Tetrame thyldiamino- 1: l’dinaphth- ylmethane and 1:l’-Tetramethyl- diaminodinaphthylmethane (Mo R- GAN), T., 823 ; P., 1900, 131. Tetramethylenedicarboxylic acid. See cycZoButanedicarboxylic acid. aa,k?B-Tetramethylglutaric acids (hcp tuncdicnrbozylic acids) ( TIIOIWE), T., 932 ; (TIIORPE aiid Yousa), T., 93G ; P., 1900, 114.Tetramethylhmmatoxylin, oxidation of (PEEKIN and YATES), P., 1900, lot. Tetramethylhaematoxylone, melting point of (GIIAODY and l’EI:KIs), P., 1899, 241. Tetramethylpyrone and its hydrate and salts (COLLIE and s,TF,ELII:), ‘l’., 961 ; P., 1900, 146. periodide (COLLIE and STEELE), T., 1114 ; P., 1900, 164. Temperature, influence of, on the specific rotation of niono- ancl di- acetyl- and -plieiiacetyl-tartrates (MCCRAE and PnTTEnsoN), T., 1106. Critical constants. See under Critical. Transition temperatures, determina- tion of (DAWSOS and WILLIAMS), l’., 1899, 210. Thermochemical data of alloys of copper and zinc (f.) (BAKER), P., 1899, 195. of ammonium cyanate (f. and t.) (WALKER and Woon), T., 27 j P., 1899, 209.Heat of solution of ammonium cyanate (WALKER and WOOD), T., 27 ; P., 1899, 209. Thetine dei,ivntivcs, resolution of (POPE and ~’EAC‘IIET), T., 1072 ; P., 1900, 12. Thiocarbamide, action of, on ethyl phenylpropiolate (1irlIEIIIANN am1 STAPrxroh’), T., 242 ; P.. 1900, 12. Tin compounds, asymmetric optically active (POPE and PEACHET), I)., 1900, 42, 116. Toluene, refraction and magnetic rotation of (PERKIS), T., 267 ; P., 1899, 237. THEltMOCIIEMISTRY :- Toluene, 2 :4:5-trichloro- (MORGAN), T., 1204. Tolyl acetyl nitrogen chlorides ant1 bromides, o- aiid p - (acetyl-chZoro- and 102. 24-Tolylenediamine, 5-chloro- and its ncetyl derivatives (MORGAX), T., 1204 ; P., 1900, 170. ~-~~~-Tolyloxycinnamic acid, aiid its ethyl ester (RUI1EsrAxN and BEDDOW), T., 1119 ; P., 1900, 165. B-Tolyloxycinnamic acids, o- and 2)-, ancl their ethyl esters (RuHesrass and EEDDOW), T., 984 ; P., 1900,123. Tolyloxyfumaric acids, o-, nt-, and $1-, and their ethyl esters (Rurmxr.\Ns and BEDDOW), T., 1124; P., 1900, 165. m-Tolyloxymaleic acid (RUHEMAXN and 13E,DDOW), T., 1125 ; P., 1900, 165. nt -To1 ylox y s t yrene (Ru HEN ANS and BEDDOW), T., 1119 ; P., 1900, 165. o- and p-Tolyloxystyrenes (RUHEMANN and BEDDOW), T., 984 ; P., 1900, 123. Triacetyljapaconitine (DUSSTAX and READ), T., 54 ; P., 1899, 207. 1:3:4-Triethylbenzene. See 4-Cumeiie. Triethylsulphine iodide mercuric iodide (SMILES), T., 162 ; P., 1899, 240. 1:3:5-Trimethylbenzene. See Mcsityl- one. 2:34-Trimethylbeneoio acid (peh?iitylic acid) (LhPWOIlTH and CHAPMAN), ‘r , 311 ; P., 1900, 4. Trimethylbrazilin, oxidation of, with potassium permanganate (GILBODY, PEILKIS, and YATES), P., 1900, 105. aSB-Trimethylbutyric acid, y-cyano-, ethyl ester (THOBPE and YOUKG), T., 939 ; P., 1900, 115. Trimethyldihydroresoreylic acid, ethyl ester and Trimethyldihydroresorcinol and its ethyl ether and bronio-derivu- tives (CROSSLET), P., 1900, 90. Trimethyldihydroxybenzenes (COLLIE and STEELE), T., 961 ; P., 1900, 146. tmm-Trimethylenedicarboxylic acid, fornintion of ( UOJVTELI, aiid PERKIS), l’., 1899, 242. aBB-Trimethylglutaric acid ( h c m i ~ e - dicnrboxylic acid) ( CIIOSSLEY), P., 1900, 91. Trimethylhydrindamine iodide, prepara- tion of, and indene from (KIPPING and HALT,), T., 469 ; P., 1900, 54. Trimethylpyrone (COLLIE niid STEELE), T., 961 ; P., 1900, 146. Trimethylsulphine iodide mercuric iodide (SMILES), T., 161 ; P., 1899, 240. -broi,to-n,,2inotoZ2cencs) (CHATThWAY and ORTOX), T., 790 ; P., 1900,INDEX OF SUBJECTS. 1363 Triphenylcarbinol, attempts to l)rel)iire ethers of (LANDER), T., 732. V. Valeric acids (a- and B-,m.dliylbictyric acids), y-cyano-, ethyl esters ( HOWLES, THOILPE, and UDALL), T., 947 ; P., 1900, 116. Vanadium, separation of, from sulphuric acid ( G o ~ u m ) , T., 1096. Vapour density of dried mercury and of dried mercurous chloride (UAKEE), T., 646 ; P., 1900, 68. Vapour pressure of camphor (ALLEN), T., 413 ; P., 1899, 135. of diisopropyl and diisobutyl (YOUNG and FORTEY), T., 1126 ; P., 1900, 165. of naphthalene (ALLEN), T., 400 ; P., 1899, 122. of moctane (YOUSG), T., 1145 ; P., 1900, 166. Vitexin, coiistitution of (PEEKIN), T., 422 ; P., 1900, 45. Volume, specific, of diisopropyl and diisobutyl (YOUNG and FOISEY), T., 1126 ; l’., 1900, 165. of n-octane (YOUXG), T., 1145; P., 1900, 166. W. Water, conductivity of, distilled in air Willow bark, new glncoside from (WALKER and CorinracIc), T., 11. (JOWE’TT), ‘r., 707 ; P., 1900, 89. X. Xylenes, o-, 1 1 1 - , and 11-, rcfractioii ant1 magnetic rotation of (PECKIN), T., 267 ; l’., 1899, 237. Xylidines, isomeric, sepai’ation of, from commercial sylidine ( HODGKIKSOK and LInwAcH), T., 65 ; P., 1899, 202. 2. Zinc alloys with copljer, heat of conibin- Zinc sulphate, combination of, with ammonia in aqueous solution (DAW- SON and MCCICAE), T., 1245 ; I?., 1900, 173. hydroximidosulphate, production of (DIVEILS and HAGA), T., 690 ; P., potassium sulphate (MALLET), T., 220 ; P., 1899, 227. ation of (BAKER), P., 1899, 195. 1900, 71.

ISSN:0368-1645    

DOI:10.1039/CT9007701343

出版商:RSC    

年代:1900

数据来源: RSC