SUBJEC~INDEX Abienol 356. Antibiotics nucleoside 483. Acetylenes 243. Aporphine alkaloids 432. Acids and bases hard and soft 146. Aristeromycin 484. Acidity functions 107. Aromatic chromaphores in cjrcular dichroism Acronycine synthesis of 427. 50. Addition of methylene iodide to alkenes 270. in optical rotatory dispersion 50. Albomycin 484. compounds photochemistry of 179. Aldgamycin E 410. molecules X-ray crystallography of 69. Aldoketens dimerisation of 264. polycylic systems 302. Aliphatic halides 267. substitution electrophilic 115 Alkaloids amaryllidaceae 433. under irradation 183. aporphine 432. Aromaticity tests for 273. aspidosperma 442. Aspidosperma alkaloids 442. cinchona 427. Asymmetric synthesis of a-amino-acids 454. ergot biosynthesis of 520.Atractyloside 359. galbulimima 447. Automerisation 135. homoaporphine 433. Aza-azulene 421. iboga 440. Azabullvalene 420. indole 434. Azapentalenes 393. biosynthesis of 522. 4-Azapentalenyl anion 388. ipecacuanha biosynthesis of 521. 5-Azapurines 41 5. isoquinoline 429. Azepines 419. lupin 425. Azetidines 381. lycopodium 445. Aziridines 376. macrocyclic bisbenzylisoquinoline 430. Aziridinium salts 378. morphine type 433. Aziridinones 378. pachysandra 446. Azirines 376. protoberberine 430. pyridine 425. Backbone rearranged products from steroids pyrrole 425. 367. pyrrolizidine 425. Bacteriophage-induced RNA replicases 508. quinoline 427. Barbaralone 346. steroidal 445. Barrelline 339. terpenoid 445. Bases and acids hard and soft 146.yohimbe 435. Benzene photochemistry of 189. Alkanes 255 photolysis of. 280. Alkanecarboxylic acids 255. Benzene oxide-oxepin equilibrium. 423 Aikenes 249. Benzodiazepinones 422. addition of methylene iodide to 270. Benzylisoquinoline alkaloids biosynthesis of Alk-7-en-2-one; cyclisation of 264. 511. Alkylations 213. Benzynes 286. Alkynes 243. Barberine conversion into columbaurine 429. Aliphatic esters 256. Bicyclo[n,l,O]alkanes 31 3. Friedel-Craft reactions 257. Bicyclobutanes 321. Alloxazines 416 Bicycloconjugation 138. Aluminium hydrides use in reduction 200. Bicyclo[2,1,1]hexanes 329. Amanitine cyclo-octapeptides 47 1. Bicyclo[2,2,0]hexanes 329. Amaryllidaceae alkaloids 433. Bicyclo[3,l,O]hexanes 327. Analytical methods for organometallic com- Bicyclo[3,2,0]heptadienes 330.pounds 220. Bicyclo[ l,l llpentanes 325. Androstanes l4a-hydroxy- dehydration of 370. Bicyclo[2,l,O]pentanes 324. Angustomycin 483 Bicyctononanes 340. Annulenes 296. Bicyclononatrienes 345. Anthropod defensive substances 350. Bicyclo-octadiene deuterium exchange with 340. Anti-aromaticity 278. Bicyclo[3,2,l]octanes 332. 568 Subject Index Bicyclo[3,3,0]octanes 332. Bicyclo[3,2,l]octenes 339. Bicyclo[4,2,0]octenones 339. Bicyclo[4,2,0]octadienone 333. Biflavanoids 414. Biosynth’esis of alkaloids 51 1. of carotenoids 527. of isoprenoids 519. of isoprenoid alkaloids 520. of sesterterpenes 522. of shikimate-derived compounds 528 of steroids 523. of terpenes 349.of triterpenoids 523. Birch reduction of free phenols 366. Bisbenzylisoquinoline alkaloids synthesis of 431. macrocyclic alkaloids 430. Bishomocubane 347. Bond order theoretical predictions of 274. Boron hydrides use in reduction 201. Bridge flipping energy burner to 135. Bullvalene 346. Butadiene nickel-catalysed dimerisation of 3 18. t-Butylsulphenic acid 261. Caerulin a new peptide 470. Caged structures 335. -Carbene cyclopropylmethyl- 3 15. dialkoxycarbonyl- 3 11. isopropylidene 3 15. Carbohydrates 404. ringcontractions in 409. Carbon-13 n.m.r. 12. Carbonium-ion rearrangements 133. Carbonium ions stable 125. studied by n.m.r. 21. Carbonyl compounds general syntheses of 210. photochemistry of 171 chromophore in circular dichroism 48.in optical rotatory dispersion 48. Carbonylation 21 1. Carboxy chromophores in optical rotatory dispersion 53. Carboxylic acids X-ray crystallography of 65. derivatives gexleral syntheses of 212 Cardenolides 372. Carotenoids biosynthesis of 527. Chalcones sodium borohydride reduction of 412. Chamigrene 354. Chemical-shift differences calculation of 5. and polar interactions 11 1. in n.m.r. 5. solvent effects on 16. Chlorophyll configurations of methyl groups in 385. Cholestane-2,3-diones benzylic rearrangements of 371. Cholesterol microbiological degradation of side-chain 373. total synthesis of 365. Cinchona alkaloids 427 Circular dichroism 47. Columbamine synthesis from berberine 429 Conessine total synthesis of 365.Conformational behaviour in pyran derivatives 404. studies by e.s.r. 32. studies by n.m.r. 20. Conformations of peptides 473. Correlation of coupling constants and molecular parameters 7. Corrins 386. Coupling constants calculation of 7. correlation with molecular parameters 7. in n.m. r. 7. long-range 8. long-range measurement of 25. sign of 9. intramolecular of aliphatic dihalides 270. Cryptowoline synthesis of 429 Cubane 346. Cumulenes cyclic 334. Cyanogen azide 259. Cyasterone 371. Cyclic cumulenes 334. molecules non-aromatic X-ray crystallo-graphy of,77. Cyclisation of alk-7-en-2-ones 264. catalytic of aliphatic compounds 334. Cycloadditions 153. subject to electrophilic catalysis 396.Cycloartenol 363. Cyclobutadienes 289. Cyclobutanes n.m.r. parameters of 11. Cyclobutanones photolysis of 321. Cyclodecapentaene 345. Cyclohexadienones rearrangement of 326. Cyclohexane pufluoro- base elimination re-actions of 326. Cyclohexenones photochemical rearrangement of 176. Cyclo-octapeptides amanitine 471. Cyclopentadiene 322. Cyclopentanoid monoterpenes biosynthesis of 519. Cyclophanes 283. Cyclopropanes 3 12. by addition of methylene iodide to alkenes 270. Cyclopropanecarboxaldehyde,3 12. Cyclopropenes 278. Cyclopropylmethylcarbene 3 15. Dialkyl disulphides oxidation of 262. Diazanorcaradienes 421. Dehydrocyclo-octatetraene,322. Dehydrogenation of steroidal 3-ketones 369.Denaturation of DNA,,SOl. Deshielding effects in n.m.r. 6. Determination ofN-terminal residuesinpeptides 455. Deuterium exchange with bicyclo-octadiene 340. Subject Index 569 Dewar benzene 281. hexamethyl 280. Dialkoxycarbonylcarbene 31 1. Diazepines 421. Dichlorocarbene insertion reactions of 270. Dielectric constant measurements of peptides 475. Digacetigenin 371. Dimerisation of aldoketens 264. of butadiene catalysed by nickel 318. catalysed of norbornadiene 337. Dimethylsulphonium methoxycarbonylmethyl- lyide 263. Dioxazoles 396. Diphenylsulphonium isopropylylid 263. 1,3-Dipoles 396. Dipyrones 41 1. Diradicals studied by e.s.r. 42. Displacements nudeophilic 152. Disulphides dialkyl oxidation of 262.Diterpenoids 356. Dithianes steroidal 370. Dithiins 417. DNA 500. breaks in strands of. 501. circularity of 502. denaturation of 501. terminal redundancy in 502. polymerase 508. Double-resonance nuclear magnetic resonance 10. 26. Ecdysones hydroxy- 371. ElcB mechanism 149. E2cB mechanism 149. Electrocyclic reactions 15 1 168. b-Elemene synthesis of 352. Elemol synthesis of 352. Electron nuclear double resonance studies 35. Electron spin resonance studies of conformations. 32. of electron transfer reactions 33. of free radicals in solids 38. of free radicals in solution 29. of ion-pairs in solution 33. of multiradicals 42. of proton transfer reactions 33. of transient radicals 34. of triplet state 42.Electron transfer reactions studied by e.s.r. 33. Electrophilic aromatic substitution 115. hydroxylation 122. substitution at positively charged substrates 119. Eliminations olefixi-forming 147. 1,3-Eliminations terminology for 151. Endor studies 35. Enzymes 506. Eperuane series 357. Ergot alkaloids biosynthesis of 520. Esters aliphatic 256. Euparotin 355. Filifolones ,352. Flash photolysis and optical rotatory dispersion combined 47. Flavans 412. Flavenes 412. Flavones 413. Fluxional molecules 346. Fragin 260. Free-energy relationships linear 113. Free radicals electron nuclear double reson-studies of 35. nuclear magnetic resonance studies of 36. in solids studied by e.s.r. 38. in solution studied by e.s.r.29. Friedel-Craft reactions aliphatic 257. Fries rearrangements under irradiation 185. Fulminic acid 258. Fulvalenes 291. Fulvenes 29 1. Furans 389. Galbulimima alkaloids 447. Germacratriene 352. Gibberellins 358. Glycosides 407. Glycosidic bond in nucleosides synthesis of,483. Glycyrrhetic acid 363. Gramicidin S conformations in 476. Grignard reagents constitution of 223. Halides,,aliphatic 267. Hard and soft acids and bases 146. Heterocyclic compounds photochemistry of 191. photoinduced rearrangements 191. five-membered rings 383. four-membered rings 381. molecules X-ray crystallography of 83. photocleavage of arylcyclopropanes 197. six-membered rings 399. three-membered rings 376.High-molecular weight RNA 499. Homoaporphine alkaloids 433. Homoaromaticity 138,274. Homoconjugation. 138. Homocubane 346. Homosemibullvalene 344. Hooplane 271. Hormones juvenile 352. Hydroboronation 201. of aliphatic halides 267. Hydrogen cyanide polymerisation of 260. Hydrogenation catalytic 199. 14a-Hydroxyandrostanes dehyration of 370. H ydroxyecdysones 371. Hydroxylation electrophilic 122. Hyperfine splitting constants 36. Iboga alkaloids 440. Ifllaiamine synthesis of 427. 5 70 Subject Index Illudol 356. Imidazoles 396 Indazoles 392. n-Inductive effects 110. Indole alkaloids 434. biosynthesis of 522. Indoles 386 388. Indolenines synthesis of 387. Insertion reactions of dichlorocarbene 270.Insulin 468. Internal rotation studied by u.m.r. 18. Intramolecular coupling of aliphatic dihalides. 270. Ion-pairs in solution studied by e.s.r. 33. Ipecacuanha alkaloids biosynthesis of $21. Iridane 351. Isoamic acid 393. Isoflavones 413. Isoprenoid alkaloids biosynthesis of 520. Isopropylidenecarbene 3 15. Isoquinoline alkaloids 429. Isotope effects primary on reaction mechanisms 99. secondary on reaction mechanisms 104. solvent on reaction mechanisms 103. Isoxazoles 396 398. Isoxazolidines 396. Isoxazolines 396. Kinetic studies by n.m.r. 17. Labdane derivatives 357. /3-Lactams 399. Lactones optical rotatory dispersion of 53. Lansic acid 360. Linear free-energy relationships 11 3. Liquid-crystal studies by n.m.r.22. Litsericine 432. Lupin alkaloids 425. Lupinine synthesis of 427. Lycopodium alkaloids 445. Malabaricol 360. Marrubiin 357. Mass spectrometry of depsipeptides 458. of small peptides 458. Mechanism of elctrophilic aromatic substi-tution 117. Meliantriol 360. Methanesulphinic acid 261. Mixed-metal organometallics 241. Modification of functional groups in aliphatic compounds by perfluorination 265. parameters correlation with coupling con-stants 7. Molecular basicity 107. Monoterpenoids 350. Morphine-type alkaloids 433. Multiradicals studied by e.s.r. 42. Nickel catalysis of the dimerisation of butadiene 318. Nitrene ethoxycarbonyl- 260. Nitrogen-atom inversion studied by n.m.r. 19. Nitrogen chromophores in circular dichroism 51.in optical rotatory dispersion 51. Nitrogen n.m.r. 14. N.I.H. shift in alkaloid biosynthesis 519. Non-aromatic cyclic molecules X-ray crystallo- graphy of 77. Norbornadienes 335. catalysed demerisation of 337. Norbornanes 336. Norbornyl cation 140. Norcaradiene-tropilidene equilibrium 339. Norcaradienes 339. 19-Norsteroids syntheses of 363. N-Terminal residues in peptides determination of 455. Nuclear magnetic resonance. assignments from nuclear Overhauser effects 24. measurements and reaction mechanisms 11 1. studies of free radicals 36. of peptides 474. Nuclear Overhauser effects and n.m.r. assign- ments 24. Nucleic acids photochemistry of 487. preparation of 493. secondary structure of 489.Nucleic acid bases 480. reaction with formaldehyde 481 selective modification of 480. specific alterations of 482. substitutions 133. Nucleophilic displacements 152. Nucleoside antibiotics 483. Nucleosides 480. synthesis of the glycosidic bond 483 Nucleotides 484. reagent specificity in methylation 484. syntheses on polymer supports 485. Octadecadeoxyribonucleotides controlled syn- thesis of 485. Qlefins 249. general synthesis of 206. photochemistry of 164. Olefin-forming eliminations 147. Oligonucleotides 485. Ophiobolane 359. Optical rotatory dispersion 47. and flash photolysis combined 47 163. measurements on peptides 474. Orcinols 411. Organoaluminium compounds 234. Organoboron compounds 227.Organogermanium compounds 238 Organolithium compounds 221. Organomagnesium compounds 224. Organomercury compounds 225. Organometallic compounds 219. containing metal-metal bonds 241 Organosilicon compounds 236. Subject Index 57 1 Organotin compounds 239. Organozinc compounds 224. Overhauser effects and n.m.r. assignments 24. Oxadiazolines 397. Oxazines 418. Oxaziridines 384. Oxazolidines 398. Oxazolones mesoionic 396. Oxepin-benzene oxide equilibrium 423. Oxetans 382. Oxetones 389. Oxidation 204. of dialkyl disulphides 262. Oximes as 1,3-dipoles 396. Oxygen-17 n.m.r. 14. Pachysandra alkaloids 446. Peptide bond cleavage of 458. formation of 462. Peptide conformations 473. Peptide synthesis 460.racemization in 466. Peptides cyclic 471. dielectric constant measurements of 475. natural 468. synthesis of 468. structural elucidation of 455. Perfluorocyclohexane base elimination reac-tions of 326. Perfluorination as a means of modifying func- tional groups in aliphatic compounds 265. Phenethylisoquinoline alkaloids biosynthesis of 515. Phenols free Birch reduction of 366. Phenol oxidation 307. Phenolic derivatives naturally occurring 41 1. Phloroglucinols 41 1. Phorbol 357. Phosphorescence excitation technique 162. Phosphorus chromophores in optical rotatory dispersion 52. Photoadditions across ethylenic double bonds 170. Photochemistry 161. nucleic acids 487. Photocleavage heterolytic of arylcyclopropanes 197.Photocylisation of Schiff bases 397. Photodimerisations 178. Photo-Fries rearrangements 185. Photolysis of benzene 279. carbonyl compounds 174. cyclobutanones 321. Photosubstitution 183. Picrotoxinin 352. Perezinone 355. Pimaric acid 357. Piperidines 399. Plinols 350. effects on reaction mechanisms 108. Polar interactions and n.m.r. chemical shifts 111. Polyclic systems aromatic 302. Polymer supports in nucleotide syntheses 485. Polynucleotide ligase 506. Polynucleotide synthesis strategy and tactics 485. Porphyrins 385. Positively charged substrates and electrophilic substitution 119. p-n Interactions 11 1. Primary isotope effects on reaction mechanisms 99. Progesterone total synthesis of 365.Propargylic alcohols conversion into vinyl halides 268. Propellatriene 346. Protecting groups for peptide synthesis 460. Protoberberine alkaloids 430. Proton transfer reactions studied by e.s.r. 33. Protolysis selective of primary C-B bond 201. Purines 415. Pyron derivatives conformational behaviours of 404. Pyrans 389. Pyranoses 404. Pyranosides 404. Pyrazines 416. Pyrazolines 39 1. Pyrazoles 392. Pyridine alkaloids 425. biosynthesis of 516. Pyridines 400. Pyrimidines 415,417. Pyrimidinethiones 415. Pyrrole alkaloids 425. Pyrrolizidine Jkaloids 425. Quinoline alkaloids 427. Quinones 307. photochemistry of 190. Racemization in peptide synthesis 466. Radicals transient studied by e.s.r.34. Reaction mechanisms 99. Rearrangements of cyclohexadienones 326. sigmatropic 159. involving carbonium ions 133. Reduction 199. Birch of free phenols 366. by use of aluminium hydrides 200. by use of boron hydrides 201. Resolution enhancement in n.m.r. 25. Ring enlargements in photolyses 401. intersion studied by n.m.r. 18. RNA 494. high-molecular weight 499. RNA polymerase. 507. R NA replicases bacteriophage-induced 508. 5s-RNA 495. t-RNA yeast phenylalanine 495. t-RNA yeast valine 495. Rotenoids synthesis of 413. 572 Subject Index Santonene 355. Schiff bases photocyclisation of 397 Secondary isotope effects on reaction mechan- isms 104. Serratene 362. Sesquiterpenoids 352. Sesterterpenoids 359.biosynthesis of 522. Shielding effects in n.m.r. 6. Shickimate-derived compounds biosynthesis of 528. Shionone 360. Showdomycin 410,484. Sigmatropic rearrangements 159. Soft and hard acids and bases 146. Solvent effects on chemical shifts 16. Solvent isotope effects on reaction mechanisms 103. Solvolysis 145. Spectropolarimeter attachment for recording fully compensated magnetic optical rotatory dispersion 47. Spin-labelling techniques in e.s.r. 37. [mnISpirarenes 277. Spiroconjugation 138 276. Stable carbonium ions 125. Stellatogenin 362. Steroidal alkaloids 445. dithianes 370. 3-ketones dehydrogenation of 369. Steroids 363. backbone rearranged productions from 367. biosynthesis of 523.Stilbene triplet 186. Stilbenes photochemistry of 186. Streptozot ocin 4 10. Substitution aromatic under irradiation 183. electrophilic aromatic 115. nucleophilic 133. effects in reaction mechanisms 108. N-Sulphonylamines 262. Sulphur chromophores in optical rotatory dis- persion 52. Sulphuranes 312. Sydnones 396. Terpenoid alkaloids 445. Tetrahydrioazepines 41 8. Tetranortriterpenes 360. Theoretical predictions of bond order 274. Thiadiazoles 397. 7-Thiapentalenyl anion 388. Thiathiophthens 395. Thiepin dioxide 423. Thietans 383. Thiophens 390. Thioketens 261. Thurberogenin 362. Toyocamycin 484. Transfer RNA 495. Triasterane 344. 1,2,3-Triazole 395 398. 1,2,4-Triazolinedione 395. Tricyclo-octanes 343.Triplet states studied by e.s.r. 42. Tripyrones 412. Triradicals 42. Triterpenoids 360. biosynthesis of 523. Tropilidene-norcaradiene equilibrium 339. Tropolones photoisomerisation of 195. Tropone photodimerisation of 195. Troponoid compounds photochemistry of 195. Tryptophan containing peptides structural elu- cidation of. 455. Ursolic acid derivatives 363. Valency isomerism studied by n.m.r. 19. Vetivones 353. Vinhaticoic acid 358. Wittig synthesis stereochemical control of 207. Wurtz-type reaction of aliphatic halides 268. X-Ray crystallography 65. Yeast phenylalanine t-RNA 495. Yeast valine t-RNA 495. Yohimbe alkaloids 435.