J O U R N A L OF THE CHEMICAL SOCIETY, TRANSACTIONS. HORACE T. BROWN, LL.D., F.R.S. J. DEWAR, LL.D., F.R.S. WYNDHAM R. DUNSTAN, M.A., F.R.S. C. E. GROVES, F.R.S. A. VERNON HARCOURT, M. A,, F.R. S. C. T. HEYCOCK, M.A., F.R.S. R. MELDOLA, F.R.S. H. FORSTEE MORLEY, M. A,, D.Sc. A. SCOTT, D.Sc., F.R.S. T. E. THORPE, LL.D., F.R.S. W. A. TILDEN, D. Sc., F. R. S. @hifor# : C. E. GROVES, F.R.S. W. P. WYNNE, D.Sc., F.R.S. Sinb-@;Mtar ; A. J. GREENAWAY. 1899. Vol. LXXV. LONDON: GURNEY & JACKSON,: 1, PATERNOSTER ROW, 1899.I ~ I C H A I ~ ~ CLAY AND BONS, LIAIITM:U LONDON AND BC’YCIAI’.C O N T E N T S. PAPERS READ BEFORE 1.-The Oxidation of Polyhydric By HENRY J. HOBSTMAN JACKSON, B.A., B.Sc. I1 .-D-Ald e bydopropionic Acid, THE CHEMICAL SOCIETY. PAGE Alcohols in Presence of Iron.FENTON, M.A., and HENBY CHO*CH;CH,*C00H. and . 1 b-Aldehydoikobutyric Acid, CHO*C~,*Cri(CH,)*COOH. By WILLIAM H. PERKIN, jun., and CHARLES H. G. SPRANKLING 111.-Cannabinol. Part I. By THOMAS BARLOW WOOD, M.A.; W. T. NEWTON SPIVEY, M.A. ; THOMAS HILL EASTERFIELD, M.A., Ph.D. . 1V.-Characterisation of Racemic Compounds. By FREDERIC STANLEY KIPPING and WILLIAM JACKSON POPE . V.-Crystalline Form of Iodoform. By WILLIAM JACESON VL-PP-Dimethylglutaric Acid and its Derivatives ; Synthesis By WILLIAM H. PERKIN, POPE . of cie- and tram-Caronic Acids. jun., and JOCELYN F. THORPE. . VII. -Sy n t hesis of apP-Trime t h y lglutaric Acid, COOH*CH(CH,)*C(CH,),*CH,*COOH. By WILLIAM H. PERKIN, jun., and JOCELYN F. THORPE . VI1I.-Occurrence of Orthohpdroxyacetophenone in the Volatile Oil of Chione glabra.By WYNDHAM R. DUNSTAN, F.R.S., and THOMAS ANDERSON HENRY, Salters’ Research Fellow in the Laboratories of the Imperial Institute 1X.-Occurrence of Hyoscyamine in the Hyoscyamus mulicus of India. By WYNDHAM R. DUNSTAN, F.R.S., and HAROLD BROWN, Assistant Chemist in the Laboratories of the Imperial Institiite . X.-Preparation of Hyponitrite from Nitrite, through Hydroxy- amidosulphonate. By EDWARD DIVERS, M.D., D.Sc., F.R.S., XI.-Absorption of Nitric Oxide in Gas Analysis. By EDWARD XI1.-Interaction of Nitric Oxide with Silver Nitrate. By . and TAMEMASA HAGA, D.Sc., F.C.S. . . . DIVERS, M.D., D.Sc., F.R.S. . EDWARD DIVERS, M.D., D.Sc., F.R.S.. A 2 11 20 36 46 4s 61 66 72 77 82 83iv CONTENTS. XII1.-Preparation of Pure Alkali Nitrites. By EDWARD DIVERS, M.D., D.Sc,, F.R.S.. . . . 8 . X1V.-Reduction of an Alkali Nitrite by an Alkali Metal. By EDWARD DIVERS, M.D., D.Sc., F.R.S. . * . 8 XV.-Hyponitrites ; their Properties, and their Preparation by Sodium or Potassium. By EDWARDIVERS, M.D., D.Sc., F.R.S. , . I . . . XV1.-Derivatives of Camphoric Acid. Part 111. By FRED- ERIC STANLEY KIPPING, Ph.D., D.Sc., F.R.S. . . XVI1,-a-Retotetrahydronaphthalene. By FREDERIC STANLEY KIPPING, Ph.D., D.Sc., F.R.S., and ALFRED HILL XVII1.-Production of Optically Active Mono- and Di-alkyl- oxyswcinic Acids from Malic and Tartaric Acids. By THOMAS PURDIE, F.R.S., and WILLIAM PITKEATHLY, B.Sc., Berry Scholar in Science . . . X1X.-Determination of the Constitution of Fatty Acids. Part I. By ARTHUR WILLIAM CROSSLEY and HENRY RONDEL LE SUEUR .. . XX.-Some Halogen Derivatives of Acetone Dicarboxylic Acid. Part 1. By FREDERICK W. DOOTSON, M.A. , . XX1.-Action of Chlorosulphonic Acid on the Paraffins and other Hydrocarbons as a means of Purifying the Normal Paraffins. By SYDNEY YOUNG, D.Sc., F.R.S. . XXI1.-Oxidation of Sulphocamphylic Acid. By W. H. PERKIN, jun. . . XXII1.-Researches on Moorland Waters. I. Acidity, By WILLIAM ACKROYD, F.I.C. . . XX1V.-The Nutrition of Yeast. Part I. By ARTHUR L. STERN, D.Sc. . . . . . XXV.-An Isomeride of Amarine. By H. LLOYD SNAPE, D.Sc., Ph.D., and ARTHUR BROOKE, Ph.D. XXV1.-Studies of the Terpenes and Allied Compounds. Nitrocamphor and its Derivatives. 1V. Nitrocamphor as an Example of Dynamic Isomerism. By T. MARTIN LOWRY, B.&.. . . XXVI1.-The Action of Ammonia on Ethereal Salts of Organic Acids. By SIEGFRIED RUHEMANN. . XXVIII.-The Changes of Volume due to Dilution of Aqueous Solutions, By EDWARD BRUCE HERSCHEL WADE, M.A. , XX1X.-Methanetrisulphonic Acid. By ERNEST HAROLD BAGINALL, B.Sc. . . XXX.-Maltodextrin : its Oxidation-Products and Constitution. B~HORACE T. BROWN, LL.D., F.R.S., and JAMES HILLS MILLAR . , PAGE 86 8’7 95 125 144 153 161 169 172 175 196 20 1 208 21 1 246 254 278 286CONTENTS. V XXX1.-Attempts to Prepare Pure Starch Derivatives through their Nitrates. By HORACE T. BROWN, LL.D., F.R.S., and JAMES HILLS MILLAR . XXXI1.-The Stable Dextrin of Starch Transformations, and its Relation to the Maltodextrins and Soluble Starch. By HORACE T. BROWN, LL.D., F.R.S., and JAMES HILLS MILLAR XXXIIL-Position Isomerism and Optical Activity ; the Methylic and Ethylic Salts of Benzoyl- and of Ortho-, Meta-, and Para-toluylmalic Acids.By PERCY FRANKLAND, Ph.D., F.R.S.,: and FREDERICK MALCOLM WRARTON, A. I.C., late Priestley Scholar in Mason University Oollege, Birmingham. XXXIV.-Some Regularities in the Rotatory Power of Homo- logous Series of Optically Active Compounds. By PERCY FRANKLAND, Ph.D., F.R.S. XXXV.-Detection and Determination of Sucrose in the Presence of Lactose. By EDWIN DOWZARD . * XXXV1.-Note on Certain Isomeric Tertiary Benzylthioureas. By AUGUSTUS EDWARDIXON, M.D. . . XXXVI1.-On LGssner’s Benzoylethyloxysulphocarbamic Acid ; and the Formation of Pseudoureas. By AUGUSTUS EDWARD DIXON,M.D. . XXXVIIL-Action of Metallic Thiocyanates on Certain Sub- stituted Carbamic and Oxamic Chlorides; and a New Method for the Production of Thiobiurets. By AUGUSTUS XXX1X.-Formation of a-Pyrone Compounds and their Trans- formation into Pyridine Derivatives.By SIEGFRIED RUHEMANN . . I . XL.-Hydrolysis of the y-Cyanides of Di-substituted Aceto- acetates. By WILLIAM TREVOR LAWRENCE . XL1.-Bromomethylfurfuraldehyde. By HENRY J. HORSTMAN FENTON, M.A., and Miss MILDRED GOSTLING, B.Sc., Bathurst Student of Newnham College . XLI1.-A Reaction of some Phenolic Colouring Matters. By ARTHUR GEORGE PERKIN, F.R.S.E. , . XLII1.-A Method of Studying Polymorphism, and on Poly- morphism as the Cause of some Thermal Peculiarities of Chloral Hydrate, XL1V.-Contribution to the Characterisation of Racemic XLV.-Etherification Constants of Substituted Acetic Acids, By JOHN J.SUDBOROUGH and LORENZO L. LLOYD , . E. DIXON, M.D. . . . . By WILLIAM JACKSON POPE Compounds. By A. LADENBURG . . w . I PAQE 308 315 337 347 371 373 375 388 41 1 41 7 423 433 455 465 467vi CONTENTS. X LV1.-The Rotatory Powers of Optically Active Methoxy- and Ethoxy-propionic Acids prepared from Active Lactic Acid. By THOMAS PURDIE, F.R.S.,and JAMES C. IRYINE, B.Sc. The Com- parative Rotatory Powers of Methylic and Ethylic Ditoluyl- glycerates. By PERCY FRANKLAND, F.R.S., and HENRY ABTON, late Priestley and Forster Scholar in M.ason Uni- versity College, Birmingham . . XLVII1.-Isomeric Fencholenic Acids. By GEORUE BERTRAM COCKBURN, B.A., B.Sc. . . XLIX.-Synthesis of some Derivatives of PP-Dipyridyl from Citrazinic Acid.By W. J. SELL, M.A., F.I.C., and H. JACKBON, B.A., B.Sc. . L.-The Condensation of Oxalic Acid and Resorcinol. By JOHN THEODORE HEWITT and ARTHUR ERNEST PITT . L1.-Synthesis and Preparation of Terebic and Terpenylic Acids. By W. TREVOR LAWRENCE . LI1.-Ethyl A mmoniumsulphite. By EDWARD DIVERS and MASATAKA OGAWA . LII1.-Ethyl Ammonium Selenite and the Non-existence of Amidoselenites (Selenosamates). By EDWARD DIVERS and SEIHACHI HADA. . L1V.-The Action of Certain Acidic Oxides on Salts of Hydroxy- acids. IV. By GEORGE GERALD HENDERSON, D.Sc., M.A., THOMAS WORKMAN ORR, and ROBERT J. GIBSON WHITEHEAD LV.-Derivatives of aa'-Dibromocarnphorsulphonic Acid. By ARTHUR LAPWORTH . LV1.-Crystalline Glycollic Aldehyde. By HENRY J. HORSTYAN FENTON, M.A., and HENRY JACKSON, B.A., B.Sc.. LVI1.-Diortho-substituted Benzoic Acids. Part IV. Form- ation of Salts from Diortho-substituted Benzoic Acids and different Organic Bases. By LORENZO L. LLOYD and JOHN J. SUDBOROUGH . . . LVI.11.-A Kew Compound of Arsenic and Tellurium. By E. C. SZARVASY, Ph.D., and C. MESSINOER, Ph.D. . LlX.-The Combustion of Carbon Disulphide. By HAROLD BAILY DIXON and EDWARD JOHN RUSSELL . LX.-The Action of Nitric Oxide on Nitrogen Peroxide. By HAROLD BAIGY DIXON and JAMES DYSART PETERKIN . LXI.--On the Mode of Burning of Carbon. By HAROLD BAILY DIXON . XLV11.-Position-Isomerism and Optical Activity. PAGE 483 493 501 507 518 527 533 537 542 558 5 75 580 597 600 613 630CONTENTS. vii LXI1.-A Study of the Absorption Spectra of Isatin, Car- bostyril, and their Alkyl Derivatives in Relation to Taut- omerism. By WALTER NOEL HARTLEY, F.R.S., and JAMEB LXIII.-Preparation of Acid Phenylic Salts of Dibasic Acids. By SAMUEL BARNETT SCHRYVER, D.Sc., Ph.D. LX1V.-Corydaline. Part TI. By JAMES J. DOBRIE, D.Sc., M.A., and ALEXANDER LAUDER . LXV.-The Relative Efficiency and Usefulness of various Forms of Shill-head for Fractional Distillation, with a Description of some new Forms possessing special Advan- tages. By SYDNEY POUNU, D.Sc., F.R.S. . LXV1,-The Salts of Dimethylpyrone, and t h e Quadrivalence of Oxygen. By J. N. COLLIE, Ph.D., F.R.S., and THOMAS TICKLE, Salters’ Company’s Research Fellow in the Research Laboratory of the Pharmaceutical Society of Great Britain LXVI1.-Chemical Examination of the Oleo-resin of Dacryodes hexandra.By ANDREW MORE, A.R.C.S. . LXVIIL-Estimation of Boric Acid mainly by Physical Processes. By A. WYNTER BLYTH , LXIX-The Blue Salt of Fehling’s Solution and other Cupro- tartrates. By ORME MASSON, M.A., D.Sc., and B. D. LXX.-The Allotropic Modifications of Phosphorus. By DAVID LEONARD CHAPMAN, B.A. . . LXX1.-Oxidation of Furfuraldehyde by Hydrogen Peroxide. By C. F. CROSS, E. J. BEVAN, and THY. HEXBERG . LXXI1.-Active and Inactive Phenylalkyloxyacetic Acids, By ALEX. MCKENZIE, M.A., D.Sc. . LXXIIL-Some Derivatives of Dimethyldihydroresorcinol. By ARTHUR WILLIAM CROSSLEP . LXXIV.-Condensation of Ethylic Salts of Acids of the Acetylene Series with Ketonic Compounds. By SIEGFRIED RUHEMANN and A. V. CUNNINGTON LXXV.-Action of Hydrogen Peroxide on Carbohydrates in the Presence of Ferrous Salts.By ROBERT SELBY MORRELL, M.A., Ph.D., and JAMES MURRAY CROFTS, B.A., B.Sc.. LXXV1.-The Action of Alkyl Haloids on Hy droxylamine. Formation of Substituted Hydroxylamines and Oxamines. By WYNDHAM R. DUNSTAN, F.R.S,, and ERNEST GOULDINa, B. sc. . . LXXVI1.-The Condensation of Ethylic Acetonedicarboxylate and Constitution of Triethylic Orcinoltricarboxylate. By DAVID SMILE8 JERDAN . * . . . . a J. DOBBIE, M.A., D.Sc. . * . . . STEELE, B.Sc. . s . . PAGE 640 661 6 70 6 79 710 7 18 722 725 734 747 753 771 778 786 792 808viii CONTENTS. LXXVII1.-The Colouring Matter of Cotton Flower8, Gor~yphm herbaceurn. Note on Rottlerin. By ARTHUR QEOEGE PERKIN, F.R.S.E. . . LXX1X.-T he Colouring Matters contained in Dyer’s Broom (Genista tinctoria) and Heather (Calluna vulgarig).By ARTHUR GEORGE PERKIN, F.R.S.E., and FREDERICK GEORGE NEWBURY . . . LXXX.-Researches on the Alkyl-substituted Succinic Acids. Part I. Methods of Preparation. By WILLIAM A. BONE and CHARLES H. G. SPRANKLINB. . . . . By FRANCIS E. FRANCIS, B.Sc., Ph.D., Lecturer in Chemistry, University LXXXI1.-Action of Light and of Oxygen on Dibenzyl Ketone. By EMILY C. FORTEY, B.Sc. LXXXII1.-The Vapour Pressures, Specific Volumes and Critical Constants of Hexamethylene. By SYDNEYOUNG, D.Sc., F.R.S., and EMILY C. FORTEY, B.Sc. LXXX1V.-The Composition and Tensions of Dissociation of the Ammoniacnl Chlorides of Cadmium. By WILLIAM ROBERT LANO, D.Sc., and ALBERT RIGAUT . . . LXXXV.-The Aluminium-Mercury Couple. Part I. Action of Sulphur Chloride on some Hydrocarbons in presence of the Couple, By JULIUS BEREND COHEN and FREDERICK WILLIAM SKIRROW, The Yorkshire College .LXXXV1.-The Aluminium-Mercury Couple. Part 11. The Action of Bromine on Organic Compounds in presence of the Couple, By JULIUS BEREND COHEN and HENRY D. LXXXVI1.-Experiments on the Constitution of Isooamphor- onic Acid. By WILLIAM HENRY PERKIN, jun., and JOCELYN FIELD THORPE . . . . . a * . LXXXVIIL-The cis- and tr~~s-~-Phenylbutane-aala,-tricarb- oxylic Acids, COOH*CH,* CH(C,H,)* CH(COOH)*CH,- COOH. By JOCELYN FIELD THORPE and WILLIAM UDALL . , LXXX1X.-Experiments on the Synthesis of Camphoric Acid. Part IT. By H. A. AUDEN, WILLIAV HENRY PERKIN, jun., and J. L. ROSE . I . . . XC.-The Action of Ethylene Dibromide and Trimethylene Di- bromide on the Sodium Compound of Ethylic Cyanacetate.By H. C. H. CARPENTER and WILLIAM HENRY PEBKIN, jun. XC1.-Influence of Substitution on Specific Rotation in the Bornylamine Series. By MARTIN ONSLOW FORSTER, Ph.D., D.Sc. b . . LXXX1.-Some Derivatives of Dibenzyl Eetone. College, Bristol . . m . . . . DAKIW, The Yorkshire College . . . PAGE 825 830 839 865 871 873 883 887 893 897 904 909 921 953CONTENTS. ix PAQI XCI1.-Studies of the Acids of the Acetylene Series. By SIEGFRIED RUHEMANN and ALFRED V. CUNNINGTON. . . 954 XCII1.-A Contribution to the Chemistry of the Mandelic Acids. By ALEX. MCKENZIE, M.A., D.Sc. . . 964 XC1V.-Non-existence of the so-called Suboxide of Phosphorus. By DAVID LEONARD CHAPMAN and F. AUSTIN LIDBURY. , 973 XCV.--The Chlorine Derivatives of Pyridine.Part 111. The Interaction of Chlorine and Pyridine Hydrochloride. By WILLIAM JAMES SELL, M.A., F.I.C., and FREDERICK WILLIAM DOOTSON, M. A. . 979 XCVI.-Homocamphoronic and Camphononic Acids. By ARTHUR LAPWORTH D.Sc., and EDGAR M. CHAPMAN, Burrough’s Scholar i n the Research Laboratory of the Pharmaceutical Society of Great Britain. . . 986 XCVI1.-The Action of Hydrogen Peroxide on Secondary and Tertiary Aliphatic Amines. Formation of Alkylated Hydroxylamines and Oxarnines. By WYNDHAM R. DUNSTAN, F.R.S., and ERNEST GOULDING, B.Sc. . . 1004 XCVIII. -Amidoamidines of the Naphthalene Series. By RAPHAEL MELDOLA, F.R.S., and PERCY PHILLIP PHILLIPS. . 1011 XC1X.-Condensations of Anhydracetonebenzil and its Ana- logues with Aldehydes.By FRANCIS R. JAPP, F.R.S., and ALEXANDER FINDLAY, M.A., B.Sc. . , 1017 C.-Triphenyloxazolone. By FRANCIS R. JAPP, F.R.S., and ALEXANDER FINDLAY, M.A., B.Sc. . . 1027 GI.-Interaction of Phenanthraquinone, Acetopheuone, and Ammonia. By FRANCIS R. JAPP, F.R.S., and ANDREW N. MELDRUM, B.Sc. . 1032 CI1.-Furfuran Derivatives from Benzoin and Phenols. By FRANCIS R. JAPP, F.R. S., and ANDREW N. MELDRUM, B.Sc. 1035 (3111.-Interaction of Benzoin with Phenylenediamines. By FRANCIS R. JAPP, F.R.S., and ANDREW N. MELDRUM, B.Sc. 1043 CIV.-A Series of Substituted Nitrogen Chlorides and their Relation to the Substitution of Halogen in Anilides and Anilines. By HUGH RYAN, M.A., 1851 Exhibition Scholar of the Queen’s College, Galway . , 1054 CV1.-The Action of Sulphuric Acid on Fenchone.By JAnrEs E. MARSH. . 1058 CVI1.-On a Method for Providing a Current of Gaseous Chloroform mixed with Air in any desired proportion, and on Methods for Estimating the Gaseous Chloroform in the Mixtures. By A. VERNON HARCOURT, M.A., F.R.S., Lee’s Reader in Chemistry a t Christ Church, Oxford . . 1060 By F. D. CHATTAWAY and K. J. P. ORTON. . 1046 CV.-Synthetical Preparation of Glucosides.x CONTENTS. PAGE CVII1.-The Application of Powerful Optically Active Acids t o the Resolution of Externally Compensated Basic Substances. Resolution of Tetrahydroquinaldine. By WILLIAM JACKSON POPE and STANLEY JOHN PEACHEY . . 1066 C1X.-The Application of Powerful Optically Active Acids to the Resolution of Externally Compensated Basic Substances. Resolution of Tetrahydroparatoluquinaldine.By WILLIAM JACKSON POPE and EDMUND MILTON RICH . . 1093 CX.-The Application of Powerful Optically Active Acids t o the Resolution of Externally Compensated Basic Substances. Resolution of Racemic Camphoroxime. By WILLIAM JACKSON POPE . . 1105 CXL-Homogeneity of Dextrolaevo-a-phenethylamine Dextro- camphorsulphonate. By WILLIAM JACKSON POPE and ALFRED WILLIAM HARVEY . I . 1110 CXI1.-A Method for Discriminating between ‘L Non-racemic ” and “ Racemic ” Liquids. By WILLIAM JACKSON POPE and STANLEY JOHN PEACHEY . . * 1111 CXII1.-The Characterisation of “ Racemic ” Liquids, By FREDERIC STANLEY RIPPING and WILLIAM JACKSON POPE . 1119 CXIV.-Asymmetric Optically Active Nitrogen Compounds. Dextro- and Laevo-a-benzylphenylallylmethylammon~um Iodides and Bromides. By WILLIAM JACKSON POPE and STANLEY JOHN PEACHEY . . 1127 CXV.-Tetrazoline. By SIEGFRIED RUHEMANN and H. E. STAPLETON, Scholar of St. John’s College, Oxford . . 1131 CXV1.-Action of Hydrolytic Agents on a-Dibromocamphor. Constitution of Bromocamphorenic Acid. By ARTHUR LAPWORTH . . 1134 CXVI1.-Camphoroxime. Part 111. Behaviour of Camphor- oxime towards Potassium Hypobromite. By MARTIN ONSLOW FORSTER, Ph.D., D.Sc. CXVII1.-Influence of an Unsaturated Linking on the Optical Activity of Certain Derivatives of Bornylamine. By MARTIN ONSLOW FORSTER, Ph.D., D.Sc. . . 1149 CXJX.-The Interact ion of Sodium Hydroxide and Benz- aldehyde. By CHAXLES ALEXANDER KOHN, Ph.D., B.Sc., and WILLIAM TRANTOM, Ph.D., B.Sc. . 1155 CXX.-The Ultra-violet Absorption Spectrum of Proteids in Relation to Tyrosine. By A. WYNTER BLYTH . . 1163 Annual General Meeting . . 1167 . 1141