455 Subject Index Aminohydroxylation, 364 a-Aminoketone, 281 4-Aminophenol, 18 A Aminothiophene, 158 Abnormal Claisen rearrangement, 1 a-Aminothiophenols, 184 Acrolein, 378 Ammonium ylide, 383 2-(Acylamino)-toluenes, 245 Angeli-Rimini hydroxamic acid Acylation, 100, 145, 200 synthesis, 9 Acyl azides, 98 ~-Anomer, 225 Acylium ion, 145, 149, 175, 177 Anomeric center, 211 a-Acyloxycarboxamides, 298 Anomeric effect, 135 a-Acyloxyketones, 17 ANRORC mechanism, 10 a-Acyloxythioethers, 327 Anthracenes, 51 Acyl transfer, 17, 42, 228, 298, 305, Anti-Markovnikov addition, 219 327,345 Amdt-Eistert homologation, 11 AIBN, 22, 23, 415 Aryl-acetylene, 66 Alder ene reaction, 2 Arylation, 253 Alder's endo rule, Ill 0-Aryliminoethers, 67 Aldol condensation, 3, 14, 26, 34, 2-Arylindoles, 38 69, 130, 147, 172, 305, Aryl migration, 31 340,396,412 Autoxidation, 69, 115, 118 Aldosylamine, 8 Auwers reaction, 13 Alkyl migration, 16, 132, 315, 443 Axial, 347 Alkylation, 144, 145 Azalactone, I 00 N-Aikylation, 162 Azides, 125, 330 Alkylidene carbene, 151 Azirine, 6, 7, 281 Allan-Robinson reaction, 4, 228 Azulene, 310 Allene, 119 1t-Allyl complex, 414 B Allylation, 213, 414 Baeyer-Drewson Allylstannane, 213 indigo synthesis, 14 Allylsilanes, 349 Baeyer-Villiger oxidation, 16, 53 Alper carbonylation, 6 Baker-Venkataraman Alpine-borane®, 262 rearrangement, 17 Aluminum phenolate, 149 Balz-Schiemann reaction, 354 Amadori rearrangement, 8 Bamberger rearrangement, 18 Amide acetal, 74 Bamford-Stevens reaction, 19 Amides, 28, 67,276,339, 356 Bargellini reaction, 20 Amidine, 316 Bartoli indole synthesis, 21 Amidoxime, 408 Barton decarboxylation, 22 Amination, 68 Harton-McCombie deoxygenation, Aminoacetal, 320 23 ~-Aminoalcohols, 409 Barton nitrite photolysis, 24 o-Aminobenzaldehyde, 147 Baylis-Hillman reaction, 26 ~-Aminocrotonate, 284 9-BBN, 262 1-Amino-1-deoxy-2-ketose, 8 Beckmann rearrangement, 28 456 Beirut reaction, 29 C-0 bond formation reac­ 1,4-Benzenediyl diradical, 33 tions, 60 Benzidine, 453 Burgess dehydrating reagent, 61 Benzil, 31 Benzilic acid rearrangement, 31 c Benzisoxazole, 217 Cadiot-Chodkiewicz coupling, 62 Benzofurazan oxide, 29 Cannizzaro dispropotionation Benzoin condensation, 32 reaction, 63, 412 p-Benzoquinone,284 Carbazoles, 54 Bergman cyclization, 33 Carbene, 11, 94, 119, 151, 310, 332, Betaine, 355 443 Biginelli pyrimidone synthesis, 34 Carbenoid, 59, 151 BINAP, 213,287 Carbonylation, 6, 223 Birch reduction, 36 Carmack mechanism, 434-435 His-acetylene, 62 Carroll rearrangement, 65 Bischler-Mohlau indole synthesis, Castro-Stephens coupling, 66 38 CBS reduction, 86 Bischler-Napieralski reaction, 39 Cephalosporins, 272 Bis(trifluoroethyl)phosphonate, 392 Chapman rearrangement, 67 Blaise reaction, 40 Chichibabin amination reaction, 10, Blanc chloromethylation reaction, 68 41 Chichibabin pyridine synthesis, 69 Boekelheide reaction, 42 Chugaev reaction, 71 Boger pyridine synthesis, 43 Chloroamine, 142 Boord reaction, 44 p-Chloroanilides, 291 Borsche-Drechsel cyclization, 45 Chlorocamphene, 279 Boulton-Katritzky rearrangement, Chloromethylation, 41 46 Chromium-vinyl ketene, 122 Bouveault aldehyde synthesis, 47 Chromones, 376 Bouveault-Blanc reduction, 48 Chromyl chloride, 129 Boyland-Sims oxidation, 49 Ciamician-Dennsted rearrangement, Bradsher reaction, 51 72 Bromination, allylic, 441 Cinchona alkaloid, 369 a-Bromination, 182 Cinnamic acid, 305 a-Bromoacid, 182 Claisen condensation, 73 Brook rearrangement, 52 Claisen rearrangement, 74 Brown hydroboration reaction, 53 Clarke-Eschweiler reductive Bucherer carbazole synthesis, 54 alkylation of amines, 76 Bucherer reaction, 56 Clemmensen reduction, 77 Bucherer-Bergs reaction, 57 Collins oxidation, 352 Buchner-Curtius-Schlotterbeck Combes quinoline synthesis, 79 reaction, 58 Conrad-Limpach reaction, 81 Buchner method of ring expansion, Conrotary electrocyclic cyclization, 59 280 Buchwald-Hartwig C-N bond and Cook-Heilbron thiazole synthesis, 82 457 Cope elimination reaction, 83 DBU, 251 Cope, oxy-Cope, anionic oxy-Cope DCC, 215, 267 rearrangements, 84 DEAD, 153, 267 Corey-Bakshi-Shibata reduction, 86 Decarboxylation, 22, 197,220,230, Corey-Chaykovsky reaction, 88 240,341,375 Corey-Fuchs reaction, 90 Dehydrating reagent, 61 Corey-Kim oxidation, 92 Demetallation, 286 Corey-Winter olefin synthesis, 93 de Mayo reaction, 105 Corey's ylide, 88 Demjanov rearrangement, 107 Cornforth rearrangement, 95 Deoxygenation, 23 Coumarin, 303 Dess-Martin periodinane oxidation, Criegee glycol cleavage, 96 109 Criegee mechanism of ozonolysis, Diaryl ketones, 163 97 Diastereomers, 209 Curtius rearrangement, 98 Diazo compounds, 58 CuTC, 239 Diazoacetates, 310 Cyanamide, 421 a-Diazoketone, 142, 443 Cyclic thionocarbonate, 93 Diazonium salt, 208, 253, 351, 409 Cyclization Diazotization, 107, 409 Bergman, 33 Dieckmann condensation, 110 Borsche-Drechsel, 45 Diels-Alder reaction, 111 Kennedy,218 Diene, 111 Myers-Saito, 277 Dienone-phenol rearrangement, 1 I 3 Nazarov, 280 Dienophile, 43, 111 Parham, 296 Diethyl phosphoryl cyanide, 447 Simonis, 376 Diethyl succinate, 396 Ueno-Stork, 415 Dihydroisoquinolines, 39 Cycloaddition, 97, 105, 117, 122, Dihydroxylation, 322, 369, 445 204, 218, 304, 337, 338, ~-Diketones, 17 369,405,438 Dimerization, 160 Cyclohexadienones, 113 Di-1t-methane rearrangement, 114 Cyclohexanone phenylhydrazone, Dimethylsulfonium methylide, 88 45 Dimethylsulfoxonium methylide, 88 Cyclopropanation, 72, 374 2,4-Dinitro-benzenesulfonyl Cyclopentenone, 280 chloride, 153 Cyclopropane, 88, 119, 132 Diradical, 33, 114, 277, 299 Disproportionation reaction, 63 D Ditin, 394 Dakin oxidation, 99 DMAP, 215 Dakin-West reaction, 100 Doebner reaction, 115 Danheiser annulation, 102 Doebner-von Miller reaction, 117 Danishefsky diene, Ill Doering-LaFlamme allene Darzens glycidic ester condensation, synthesis, 119 103 Dornow-Wiehler isoxazole Davis chiral oxaziridine reagent, synthesis, 120 104 Dotz reaction, 122 458 Dowd ring expansion, 123 Fleming oxidation, 140 Dutt-Wormall reaction, 125 Formaldehyde, 76 Formalin, 41 E Formic acid, 76, 237 E1, 339 Formylation, 47, 157 E1cb, 169,172,249 Forster reaction, 142 E2,27,49,305 Frater-Seebach alkylation, 144 Eglinton reaction, 126 Friedel-Crafts reaction, 145, 175, Ei, 61, 83, 403 397 Electrocyclic ring opening, 59, 310 Friedlander synthesis, 147 Electrocyclization, 33, 81, 280 Fries rearrangement, 149 Electrophilic addition, 145, 378 Fritsch-Buttenberg-Wiechell Enamine, 69, 79, 319,398 rearrangement, 151 Ene reaction, 2, 129 Fructose, 3 72 Enediyne, 33 Fujimoto-Belleau reaction, 152 Enol phosphate, 307 Fukuyama amine synthesis, 153 Enolsilanes, 345 Furans, 294 Episulfone, 328 Epoxidation G Corey-Chaykovsky, 88 Gabriel synthesis, 155, 203 Jacobsen-Katsuki, 204 Gassman indole synthesis, 156 Prilezhaev, 323 Gattermann-Koch reaction, 157 Sharpless, 366 Gewald aminothiophene synthesis, Shi, 372 158 a,f3-Epoxyketones, 128 Glaser coupling, 160 erythro, 198 Glycol, 96 Equatorial, 347 Glycosidation, 211, 225, 357 Eschenmoser coupling reaction, 127 Glycosylamine, 8 Eschenmoser' s salt, 246 Glycidic esters, 103 Eschenmoser-Clrusen, 74 Gomberg-Bachmann reaction, 161 Eschenmoser-Tanabe Gribble indole reduction, 162 fragmentation, 128 Gribble reduction of diary! ketones, Esterification, 362 163 Etard reaction, 129 Grignard reaction, 164 Evans aldol reaction, 130 Grob fragmentation, 166, 248 Grubbs' reagent, 337 F Guareschi-Thorpe condensation, Favorskii rearrangement, 132 168 Feist-Benary furan synthesis, 134 Ferrier rearrangement, 135 H Finkelstein reaction, 136 Hajos-Wiechert reaction, 169 Fischer-Hepp rearrangement, 137 Haller-Bauer reaction, 171 Fischer indole synthesis, 138 13-Haloalkoxide, 44 Fischer esterification, 139 N-Haloamines, 193 Fischer-Speier esterification, 139 Haloform, 238 Flavones, 4 Halogen-metal exchange, 151, 296 459 Hantzsch pyridine synthesis, I72 Hydride transfer, 9, 63, 254, 262, Hantzsch pyrrole synthesis, I74 290, 38I, 4II, 4I2 Haworth reaction, I75 Hydroboration, 53 Hayashi rearrangement, I77 Hydrogenation, 287 Heck reaction, I79 Hydroquinone, I22 Hegedus indole synthesis, I8I Hydroxamic acid, 9 Hell-Volhardt-Zelinsky reaction, Hydroxylation, I04 I82 ~-Hydroxyesters, I44 Hemiaminal, 341, 38I 5-Hydroxylindole, 284 Henry reaction, I83 2-Hydroxymethylpyridine, 42 Herz reaction, I84 a-Hydroxysilane, 52 Heteroaryl Heck reaction, I86 Hetero-Diels-Alder reaction, 43, I 112 Imination, 386 Heterodiene, II2 Imine, 69, 79, 117, 295, 311, 320, Heterodienophile, II2 416 Heterolytic cleavage, 279 Iminium ion, 237, 317, 319, 399 Hexacarbonyldicobalt, 286 Indanes, 310 Hexamethylenetetramine, 38I Indole, 21, 38, 45, 138, 156, 162, Hiyama cross-coupling reaction, 181,235,245,284 I87 Indigo, 14, I5 Hoch-Campbell reaction, I89 lng-Manske procedure, 203 Hodges-Vedejs metallation of o-Iodoaniline, 235 oxazoles, I9I Iodoform, 238 Hofmann elimination, 450 lndolinone, 397 Hofmann rearrangement, I92 Iodonium ion, 322, 445 Hofmann degradation reaction, I92 Ipso, 49, 256 Hofmann-LOffler-Freytag reaction, Ireland-Claisen rearrangements, 75 I93 Isocyanate intermediate, 98, 192, Hofmann-Martius reaction, I94 240 Homocoupling, 160,244,418 Isocyanide, 298,416 Homologation, II, 58, 90, 443 Isoflavones, 4 Homolytic cleavage, 24, I93, 202, Isoquinolines, II5, 3I2, 3I4, 320, 242,374,389,44I 334 Hooker oxidation, I96 Isoxazoles, I20 Horner-Wadsworth-Emmons reaction, I98, 25I J Hosomi-Sakurai reaction, 349 Jacobsen-Katsuki epoxidation, 204 Houben-Hoesch synthesis, 200 Jacobsen rearrangement, 206 Hunsdiecker reaction, 202 Japp-Klingemann hydrazone Hydantoin, 57 synthesis, 208 Hydrazines, 54, 203,