Alder ene reaction 1 Aldol condensation 3 Algar—Flynn-Oyamada reaction 6 Allan-Robinson reaction 8 Arndt-Eistert homologation 10 Baeyer-Villiger oxidation 12 Baker-Venkataraman rearrangement 14 Bamford—Stevens reaction 16 Barbier coupling reaction 18 Bartoli indole synthesis 20 Barton radical decarboxylation 22 Barton-McCombie deoxygenation 24 Barton nitrite photolysis 26 Batcho-Leimgruber indole synthesis 28 Baylis—Hillman reaction 30 Beckmann rearrangement 33 Abnormal Beckmann rearrangement 34 Benzilic acid rearrangement 36 Benzoin condensation 38 Bergman cyclization 40 Biginelli pyrimidone synthesis 42 Birch reduction 44 Bischler-Möhlau indole synthesis 46 Bischler—Napieralski reaction 48 Blaise reaction 50 Blum-Ittah aziridine synthesis 52 Boekelheide reaction 54 Boger pyridine synthesis 56 Borch reductive amination 58 Borsche-Drechsel cyclization 60 Boulton—Katritzky rearrangement 62 Bouveault aldehyde synthesis 64 Bouveault-Blanc reduction 65 Bradsher reaction 66 Brook rearrangement 68 Brown hydroboration 70 Bucherer carbazole synthesis 72

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Bucherer reaction 74 Bucherer-Bergs reaction 76 Büchner ring expansion 78 Buchwald-Hartwig amination 80 Burgess dehydrating reagent 84 Burke boronates 87 Cadiot-Chodkiewicz coupling 90 Camps quinoline synthesis 92 Cannizzaro reaction 94 Carroll rearrangement 96 Castro-Stephens coupling 98 Chan alkyne reduction 100 Chan-Lam C-X coupling reaction 102 Chapman rearrangement 105 Chichibabin pyridine synthesis 107 Chugaev reaction 110 Ciamician—Dennsted rearrangement 112 Claisen condensation 113 Claisen isoxazole synthesis 115 Claisen rearrangement 117 /?ara-Claisen rearrangement 119 Abnormal Claisen rearrangement 121 Eschenmoser-Claisen amide acetal rearrangement 123 Ireland-Claisen (silyl ketene acetal) rearrangement 125 Johnson-Claisen (orthoester) rearrangement 127 Clemmensen reduction 129 Combes quinoline synthesis 131 Conrad-Limpach reaction 133 Cope elimination reaction 135 Cope rearrangement 137 Anionic oxy-Cope rearrangement 138 Oxy-Cope rearrangement 140 Siloxy-Cope rearrangement 141 Corey-Bakshi-Shibata (CBS) reagent 143 Corey-Chaykovsky reaction 146 Corey-Fuchs reaction 148 Corey—Kim oxidation 150 Corey-Nicolaoumacrolactonization 152 Corey-Seebach reaction 154 Corey-Winter olefin synthesis 156 Criegee glycol cleavage 159 Criegee mechanism of ozonolysis 161 Curtius rearrangement 162 Dakin oxidation 165 Dakin—West reaction 167 Darzens condensation 169 XIII

Delépine aminé synthesis 171 de Mayo reaction 173 Demjanov rearrangement 175 Tiffeneau-Demjanov rearrangement 177 Dess-Martin periodinane oxidation 179 Dieckmann condensation 182 Diels-Alder reaction 184 Inverse electronic demand Diels-Alder reaction 186 Hetero-Diels-Alder reaction 187 Dienone-phenol rearrangement 190 Di-rc-methane rearrangement 192 Doebner quinoline synthesis 194 Doebner-von Miller reaction 196 Dötz reaction 198 Dowd-Beckwith ring expansion 200 Dudley reagent 202 Erlenmeyer-Plöchl azlactone synthesis 204 Eschenmoser's salt 206 Eschenmoser-Tanabe fragmentation 208 Eschweiler-Clarke reductive alkylation of amines 210 Evans aldol reaction 212 Favorskii rearrangement 214 Quasi-Favorskii rearrangement 217 Feist-Bénary turan synthesis 218 Ferner carbocyclization 220 Ferner glycal allylic rearrangement 222 Fiesselmann thiophene synthesis 225 Fischer indole synthesis 227 Fischer oxazole synthesis 229 Fleming-Kumada oxidation 231 Tamao-Kumada oxidation 233 Friedel-Crafts reaction 234 Friedel-Crafts acylation reaction 234 Friedel-Crafts alkylation reaction 236 Friedländer quinoline synthesis 238 Fries rearrangement 240 Fukuyama amine synthesis 243 Fukuyama reduction 245 Gabriel synthesis 246 Ing-Manske procedure 249 Gabriel-Colman rearrangement 250 Gassman indole synthesis 251 Gattermann-Koch reaction 253 Gewald aminothiophene synthesis 254 Glaser coupling 257 Eglinton coupling 259 XIV

Gomberg-Bachmann reaction 262 Gould-Jacobs reaction 263 Grignard reaction 266 Grob fragmentation 268 Guareschi—Thorpe condensation 270 Hajos- Wiechert reaction 271 Haller-Bauer reaction 273 Hantzsch dihydropyridine synthesis 274 Hantzsch pyrrole synthesis 276 Heck reaction 277 Heteroaryl Heck reaction 280 Hegedus indole synthesis 281 Hell-Volhard-Zelinsky reaction 282 Henry nitroaldol reaction 284 Hinsberg synthesis of thiophene derivatives 286 Hiyama cross-coupling reaction 288 Hofmann rearrangement 290 Hofmann-Löffier-Freytag reaction 292 Horner-Wadsworth—Emmons reaction 294 Houben-Hoesch synthesis 296 Hunsdiecker-Borodin reaction 298 Jacobsen-Katsuki epoxidation 300 Japp—Klingemann hydrazone synthesis 302 Jones oxidation 304 Collins-Sarett oxidation 305 PCC oxidation 306 PDC oxidation 307 Julia-Kocienski olefination 309 Julia—Lythgoe olefination 311 Kahne glycosidation 313 Knoevenagel condensation 315 Knorr pyrazole synthesis 317 Koch-Haafcarbonylation 319 Koenig-Knorr glycosidation 320 Kostanecki reaction 322 Kröhnke pyridine synthesis 323 Kumada cross-coupling reaction 325 Lawesson's reagent 328 Leuckart-Wallach reaction 330 Lossen rearrangement 332 McFadyen—Stevens reduction 334 McMurry coupling 335 Mannich reaction 337 Martin's sulfurane dehydrating reagent 339 Masamune—Roush conditions 341 Meerwein's salt 343 XV

Meerwein-Ponndorf-Verley reduction 345 Meisenheimer complex 347 [1,2]-Meisenheimer rearrangement 349 [2,3]-Meisenheimer rearrangement 350 Meyers oxazoline method 351 Meyer-Schuster rearrangement 353 Michael addition 355 Michaelis- Arbuzov phosphonate synthesis 357 Midland reduction 359 Minisci reaction 361 Mislow-Evans rearrangement 363 Mitsunobu reaction 365 Miyaura borylation 368 Moffatt oxidation 370 Morgan-Walls reaction 371 Mori-Ban indole synthesis 373 Mukaiyama aldol reaction 375 Mukaiyama Michael addition 377 Mukaiyama reagent 379 Myers—Saito cyclization 382 Nazarov cyclization 383 Neber rearrangement 385 Nef reaction 387 Negishi cross-coupling reaction 389 Nenitzescu indole synthesis 391 Newman-Kwart reaction 393 Nicholas reaction 395 Nicolaou dehydrogenation 397 Noyori asymmetric hydrogénation 399 Nozaki-Hiyama-Kishi reaction 401 Nysted reagent 403 Oppenauer oxidation 404 Overman rearrangement 406 Paal thiophene synthesis 408 Paal-Knorr turan synthesis 409 Paal-Knorr pyrrole synthesis 411 Parham cyclization 413 Passerini reaction 415 Paterno-Büchi reaction 417 Pauson-Khand reaction 419 Payne rearrangement 421 Pechmann coumarin synthesis 423 Perkin reaction 424 Petasis reaction 426 Petasis reagent 428 Peterson olefination 430 XVI

Pictet-Gams isoquinoline synthesis 432 Pictet-Spengler tetrahydroisoquinoline synthesis 434 Pinacol rearrangement 436 Pinner reaction 438 Polonovski reaction 440 Polonovski-Potier rearrangement 442 Pomeranz-Fritsch reaction 444 Schlittler-Müller modification 446 Prévost frans-dihydroxylation 447 Prins reaction 448 Pschorr cyclization 450 Pummerer rearrangement 452 Ramberg-Bäcklund reaction 454 Reformatsky reaction 456 Regitz diazo synthesis 458 Reimer-Tiemann reaction 460 Reissert reaction 461 Reissert indole synthesis 463 Ring-closing metathesis (RCM) 465 Ritter reaction 468 Robinson annulation 470 Robinson-Gabriel synthesis 472 Robinson-Schöpf reaction 474 Rosenmund reduction 476 Rubottom oxidation 478 Rupe rearrangement 480 Saegusa oxidation 482 Sakurai allylation reaction 484 Sandmeyer reaction 486 Schiemann reaction 488 Schmidt rearrangement 490 Schmidt's trichloroacetimidate glycosidation reaction 492 Shapiro reaction 494 Sharpless asymmetric amino hydroxylation 496 Sharpless asymmetric dihydroxylation 499 Sharpless asymmetric epoxidation 502 Sharpless olefin synthesis 505 Simmons-Smith reaction 507 Skraup quinoline synthesis 509 Smiles rearrangement 511 Truce-Smile rearrangement 513 Sommelet reaction 515 Sommelet-Hauser rearrangement 517 Sonogashira reaction 519 Staudinger ketene cycloaddition 521 Staudinger reduction 523 XVII

Stetter reaction 525 Still-Gennari phosphorate reaction 527 Stille coupling 529 Stille-Kelly reaction 531 Stobbe condensation 532 Strecker amino acid synthesis 534 Suzuki-Miyaura coupling 536 Swern oxidation 538 Takai reaction 540 Tebbe olefination 542 TEMPO oxidation 544 Thorpe-Ziegler reaction 546 Tsuji-Trost allylation 548 Ugi reaction 551 Ullmann coupling 554 van Leusen oxazole synthesis 556 Vilsmeier-Haack reaction 558 Vinylcyclopropane—cyclopentene rearrangement 560 von Braun reaction 562 Wacker oxidation 564 Wagner-Meerwein rearrangement 566 Weiss-Cook reaction 568 Wharton reaction 570 White reagent 572 Willgerodt-Kindler reaction 576 Wittig reaction 578 Schlosser modification of the Wittig reaction 580 [1,2]-Wittig rearrangement 582 [2,3]-Wittig rearrangement 584 Wohl-Ziegler reaction 586 Wolff rearrangement 588 Wolff-Kishner reduction 590 Woodward cis-dihydroxylation 592 Yamaguchi esterification 594 Zincke reaction 596

Subject Index 599

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