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 , 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 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 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 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 reaction, 53 Clarke-Eschweiler reductive Bucherer carbazole synthesis, 54 alkylation of , 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 , 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 , 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 , 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 , 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 , 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 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 , 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 , 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 , 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, 432, 444 Johnson-Claisen, 74 H ydrazones, 208 Jones oxidation, 352 ~-Hydride elimination, 270, 384, Julia-Lythgoe olefination, 209 424 460

K McMurry coupling, 244 Kahne glycosidation, 211 Macrolactonization, 215 Keck stereoselective allylation, 213 Madelung indole synthesis, 245 Keck macrolactonization, 215 Mannich reaction, 246 Kemp elimination, 217 Marshall boronate fragmentation, Kennedy oxidative cyclization, 218 248 Ketene, 11, 122, 443 Martin's sulfurane dehydrating 13-Ketoesters, 40, 65, 81, 230, 303, reagent, 249 376 Masamune-Roush conditions, 251 1,4- Ketones, 294 m-CPBA, 16, 323 y-Ketoolefin, 65 Meerwein arylation, 253 keto-oxazoles, 95 Meerwein-Ponndorf-Verley Ketose, 8 reduction, 254 Ketoxime, 281 Meinwald rearrangement, 255 Ketyl, 48 Meisenheimer complex Kharasch , 219 (Meisenheimer-Jackson Knoevenagelcondensation,220 salt), 153, 256, 380 Knorr pyrrole synthesis, 222 Meisenheimer rearrangement, 258 Koch carbonylation reaction, 223 Metallacyclobutene, 122 Koch-Haaf carbonylation reaction, Metallacyclopentenone, 122 223 2-Methylpyridine N-oxide, 42 Koenig-Knorr glycosidation, 225 2-Methylquinoline, 117 Kolbe electrolytic coupling, 227 Meyer-Schuster rearrangement, 259 Kolbe-8chmitt reaction, 226 Michael addition, 260 Kostanecki reaction, 228 Michael-s tetter reaction, 387 Krapcho decarboxylation, 230 Michaelis-Arbuzov phosphonate Krohnkereaction,231 synthesis, 261 Kumada cross-coupling reaction, Midland reduction, 262 233 Migration aptitude, 16 Miller-Loudon-snyder nitrile L synthesis, 263 Lactonization, 396 Mislow-Evans rearrangement, 264 Lapachol, 196 Mitsunobu reaction, 153, 265 Larock indole synthesis, 235 Miyaura boration reaction, 266 Lawesson's reagent, 236 Moffatt oxidation, 267 Leuckart-Wallach reaction, 237 Morgan-Walls reaction, 269 Lieben haloform reaction, 238 Mori-Ban indole synthesis, 270 Liebeskind-8rogl coupling, 239 Morin rearrangement, 272 2-Lithiooxazole, 191 Morpholinones, 20 LTMP, 191 Mukaiyama aldol reaction, 274 Lossen rearrangement, 240 Mukaiyama esterification, 275 Luche reduction, 241 Myers-Saito cyclization, 277

M N McFadyen-stevens reduction, 242 Nametkin rearrangement, 279 McLafferty rearrangement, 243 Naphthols, 54, 56 461

~-Naphthylamines, 56 Dakin, 99 Nazarov cyclization, 280 Dess-Martin, 109 Neher rearrangement, 281 Etard, 129 Nef reaction, 282 Fleming, 140 Negishi cross-coupling reaction, Hooker, 196 283 Jones, 351 Neighboring group assistance, 322, Moffatt, 267 358,445 Oppenauer, 290 Nenitzescu indole synthesis, 284 PCC, 351 Nicholas reaction, 286 PDC, 351 Nitric oxide radical, 24 Prilezhaev, 323 Nitrile synthesis, 263 Riley, 336 Nitrilium ion, 356 Rubottom, 345 Nitrite ester, 24 Sarett, 351 Nitroaldol reaction, 183 Swem, 402 Nitroalkane, 282 Tamao-Kumada, 404 o-Nitrobenzaldehyde, 14 Wacker, 424 a-Nitro-esters, 120 Oximes, 28 Nitronates, 183 y-Oximino , 24 N-Nitroso-anilines, 137 a-Oximinoketones, 142 Nitroso intermediate, 24, 137 Oxone, 372 Norrish type II cleavage, 243 Oxonium ion, 211,225 Noyori asymmetric hydrogenation, 287 p Nozaki-Hiyama-Kishi reaction, 289 Paal-Knorr furan synthesis, 294 Paal-Knorr pyrrole synthesis, 295 0 Palladation, 181,424 Octacarbonyl dicobalt, 300 Parham cyclization, 296 Oppenauer oxidation, 290 Passerini reaction, 298 Organoborane, 53 Patemo-Biichi reaction, 299 Organostannanes, 393 Pauson-Khand reaction, 300 Orthoester, 74 Payne rearrangement, 302 Orton rearrangement, 291 PCC, 351 Overman rearrangement, 293 PDC, 351 Oxaborolidines, 86 Pechmann condensation, 303 Oxazete, 67 Pechmann pyrazole synthesis, 304 Oxaziridine, 104 Penicillin sulfoxides, 272 Oxazole, 191 Periodinane, 109 Oxazolidinone, 130 Perkin reaction, 305 Oxazolone intermediate, 100 Perkow reaction, 307 Oxetane, 299 Perrhenate, 218 Oxidation Persulfate, 49 Baeyer-Villiger, 16 , 308 Boyland-Sims, 49 Petasis a1kenylation, 405 Collins, 351 Pfau-Plattner azulene synthesis, 310 Corey-Kim, 92 Pfitzinger quinoline synthesis, 311 462

~-Phenethylamides, 39 Rearrangement N-Phenylhydroxylamine, 18 Abnormal Claisen, I Phosphonares, 198,251,261 Amadori, 8 Phosphorus ylide, 322 anionic oxy-Cope, 84 Photolysis, 114 Baker-Venkataraman, 17 Phthalimide, 155, 203 Bamberger, 18 Pictet-Gams isoquinoline synthesis, Beckmann, 28 312 Benzilic acid, 31 Pictet-Hubert reaction, 269 Boulton-Katritzky, 46 Pictet-Spengler isoquinoline Brook, 52 synthesis, 314 Carrol, 65 Pinacol rearrangement, 315 Chapman, 67 Pinner synthesis, 316 Ciamician-Dennsted, 72 Piperazinones, 20 Claisen, 74 Polonovski reaction, 317 Cope, 84 Polonovski-Potier rearrangement, Cornforth, 95 319 Curtius, 98 Pomeranz-Fritsch reaction, 320 Demjanov, 107 Prevost trans-dihydroxylation, 322 Dienone-phenol, 113 Prilezhaev reaction, 323, 345 Di-1t-methane, 114 Primary ozonide, 97 Eschenmoser-Claisen, 74 Prins reaction, 324 Favorskii, 132 (S)-(-)-Proline, 169 Ferrier, 135 Propargyl alcohol, 235 Fischer-Hepp, 137 Propargylcation,286 Fries, 149 Pschorr ring closure, 325 Fritsch-Buttenberg-Wiechell, Pummerer rearrangement, 327 151 Pyrazoles, 304 Hayashi, 177 Pyrazolone, 422 Hofmann, 192 Pyridine synthesis, 43, 69, 172, 231 Ireland-Claisen, 75 2-Pyridone, 168 Jacobsen, 206 Pyrimidone, 34 Johnson-Claisen, 74 Pyrrole, 72, 174, 222, 295 Lossen, 240 Meinwald, 255 Q Meisenheimer, 258 Quasi-Favorskii rearrangement, 132 Meyer-Schuster, 259 Quinoline-4-carboxylic acids, 311 Mislow-Evans, 264 Quinolines, 79, 117, 147,311,378 Morin, 272 Quinolin-4-ones, 81 Nametkin, 279 Quinoxaline-1 ,4-dioxide, 29 Neher, 281 Orton, 291 R Overman, 293 Radical anion, 36, 48 oxy-Cope, 84 Ramberg-Backlund olefin synthesis, Payne,302 328 Pinacol, 315 Pummerer, 327 463

Rupe, 346 Ritter reaction, 339 Quasi-Favorskii, 132 Robinson annulation, 152, 340 Rei:!y-Hickinbottom, 194 Robinson-SchOpf reaction, 341 Schmidt, 356 Rosenmund reduction, 343 Smiles, 380 Roush allylboronate reagent, 344 Sommelet-Hauser, 383 Rubottom oxidation, 345 Stevens, 389 Rupe rearrangement, 346 Stieglitz, 390 Rychnovsky polyol synthesis, 347 Tiemann, 408 Tiffeneau-Demjanov, 409 s Wagner-Meerwein, 426 Sakurai allylation reaction, 349 Wallach,427 Salicylonitrile, 217 Wolff, 443 Sandmeyer reaction, 351 Zinin, 453 Sarett oxidation, 352 addition, 289 Schiemann reaction, 354 Reduction Schiff base, 81, 117 Birch, 36 Schilittle-Mtiller modification of the Bouveault-Blanc, 48 Pomeranz-Fritsch reaction, CBS, 86 321 Indole, 162 Schlosser modification of the Wittig Diaryl ketones, 163 reaction, 355 Luche, 241 Schmidt reaction, 356 McFadyen-Stevens,242 Schmidt's trichloroacetimidate Meerwein-Ponndorf-Verley, 254 glycosidation reaction, 357 Midland, 262 Schmittel cyclization, 277 Staudinger, 386 Scholl reaction, 359 Wharton,432 Schopf reaction, 361 Wolff-Kishner, 444 Schotten-Baumann reaction, 362 Reductive alkylation, 76 Schrock reagent, 337 Reductive amination, 237 ~-Scission, 23 Reformatsky reaction, 329 Secondary ozonide, 97 Regitz diazo synthesis, 330 Selenium dioxide, 336 Reilly-Hickinbottom rearrangement, Semidine rearrangement, 453 194 , 19, 363 Reimer-Tiemann reaction, 332 Sharpless asymmetric Reissert reaction, 334 aminohydroxylation, 364 Retro-aldol, 105 Sharpless asymmetric epoxidation, Retro-Diels-Alder reaction, 43 366 Retropinacol rearrangement, 279 Sharpless dihydroxylation, 369 Reverse electronic demand Diels- Shi asymmetric epoxidation, 372 Alder reaction, Ill Silyl enol ether, 274 Rhodium carbenoid, 59 Silyl ester, 75 Riley oxidation, 336 Silyl ether, 52 Ring-closing metathesis, 337 Simmons-Smith reaction, 374 Ring closure, 10, 110, 228 Simonini reaction, 375 Ring expansion, 59 Simonis chromone cyclization, 376 464

Single electron transfer, 36, 48, 209, Thiazolium, 387 244 Thiazothionium chlorides, I84 Singlet diradical, 299 Thiirane, 88 Skraup quinoline synthesis, 117, 378 Thiirene, 435 Smiles rearrangement, 380 Thiocarbonyl, 22, 23 SN1. 211 1,1 '-Thiocarbonyldiimidazole, 93 SN2', 307 Thioesters, 239 SNAr,67,68,256,263,380 Thiophile, 127 Sodium borohydride, 162 Thorpe-Ziegler reaction, 407 Sodium cyanoborohydride, 162 Threo, I98 Sommelet reaction, 381 Tiemann rearrangement, 408 Sommelet-Hauser rearrangement, Tiffeneau-Demjanov 383 rearrangement, 409 Sonogashira reaction, 384 Tishchenko reaction, 4II Staudinger reaction, 386 Tollens reaction, 4I2 Stetter reaction, 387 Tosyl ketoxime, 28I Stevens rearrangement, 389 Transmetallation, 233, 234, 239, Stieglitz rearrangement, 391 266,283,289,384,393, Still-Gennari phosphonate reaction, 394,401 392 Triacetoxyperiodinane, I 09 Stille coupling, 393 Trichloroacetimidate, 293, 357 Stille-Kelly reaction, 394 2,4,6-Trichlorobenzoyl chloride, Stobbe condensation, 396 448 Stolle synthesis, 397 Trimethylphosphite, 93 Stork enamine reaction, 398 Trimethylsilylallene, I02 Strecker amino acid synthesis, 399 Trimethylsilylcyclopentene, 102 Sulfenic acid, 272 Tropinone, 341 Sulfones, 209 Triplet diradical, 299 Sulfonium ion, 156 Tsuji-Trost allylation, 4I4 N-Sulfonyloxaziridines, I 04 Sulfur, 158 u Sulfur ylide, 402 Ueno-Stork cyclization, 415 Suzuki coupling, 40I Ugi reaction, 4I6 Swern oxidation, 402 Ullmann reaction, 4I8 Urea, 34 T Tamao-Kumada oxidation, 404 v Tartrate allyl boronate, 344 Vilsmeier-Haack reaction, 419 Tebbe olefination, 405 Vinylcyclopropane, 114 Terminal , 90 von Braun reaction, 42I Tetrahydrocarbazole, 45 von Richter reaction, 422 Tetrahydroisoquinolines, 314 Tetralone, I75 w TFAA,42 Wacker oxidation, I81, 424 TFP, 239 Wagner-Meerwein rearrangement, Thiamide, I27, 433 426 465

Wallach rearrangement, 427 Weinreb amide, 428 Weiss reaction, 429 Wenker aziridine synthesis, 431 Wharton oxygen transposition reaction, 432 Willgerodt-Kindler reaction, 433 Williamson ether synthesis, 437 , 198, 438 [ 1,2]- Wittig rearrangement, 439 [2,3]-Wittig rearrangement, 440 Wohl-Ziegler reaction, 441 Wolff rearrangement, 443 Wolff-Kishner reduction, 444 Woodward cis-dihydroxylation, 445 Wurtz reaction, 446

X Xanthate, 71 y Yamada coupling reagent, 447 Yamaguchi esterification, 448 z Zaitsev elimination, 450 Zincke reaction, 451 Zinin benzidine rearrangement, 453 Zwitterionic peroxide, 97