Name reactions : a collection of detailed reaction mechanisms and synthetic applications

The fourth edition is revolutionary in comparison to the previous three editions. The format change has doubled the space to accommodate at least two to three real case applications in synthesis for each name reaction. The references are updated to 2009. Several new name reactions and reagents are included to reflect the state-of-the-art of organic chemistry. Unlike other books on name reactions in organic chemistry, Name Reactions, A Collection of Detailed Reaction Mechanisms and Synthetic Applications focuses on their mechanisms. It covers over 300 classical as well as contemporary name reactions. Each reaction is delineated by its detailed step-by-step, electron-pushing mechanism, supplemented with the original and the latest references, especially review articles. Now with addition of many synthetic applications, it is not only an indispensable resource for senior undergraduate and graduate students for learning and exams, but also a good reference book for all organic chemists interested in name reactions. Front Matter....Pages i-xvii Alder ene reaction....Pages 1-2 Aldol condensation....Pages 3-5 Algar— Flynn— Oyamada Reaction....Pages 6-7 Allan–Robinson reaction....Pages 8-9 Arndt—Eistert homologation....Pages 10-11 Baeyer–Villiger oxidation....Pages 12-13 Baker–Venkataraman rearrangement....Pages 14-15 Bamford–Stevens reaction....Pages 16-17 Barbier coupling reaction....Pages 18-19 Bartoli indole synthesis....Pages 20-21 Barton radical decarboxylation....Pages 22-23 Barton–McCombie deoxygenation....Pages 24-25 Barton nitrite photolysis....Pages 26-27 Batcho–Leimgruber indole synthesis....Pages 28-29 Baylis–Hillman reaction....Pages 30-32 Beckmann rearrangement....Pages 33-35 Benzilic acid rearrangement....Pages 36-37 Benzoin condensation....Pages 38-39 Bergman cyclization....Pages 40-41 Biginelli pyrimidone synthesis....Pages 42-43 Birch reduction....Pages 44-45 Bischler–Möhlau indole synthesis....Pages 46-47 Bischler–Napieralski reaction....Pages 48-49 Blaise reaction....Pages 50-51 Blum–Ittah aziridine synthesis....Pages 52-53 Boekelheide reaction....Pages 54-55 Boger pyridine synthesis....Pages 56-57 Borch reductive amination....Pages 58-59 Borsche–Drechsel cyclizations....Pages 60-61 Boulton–Katritzky rearrangement....Pages 62-63 Bouveault aldehyde synthesis....Pages 64-64 Bouveault—Blanc reduction....Pages 65-65 Bradsher reaction....Pages 66-67 Brook rearrangement....Pages 68-69 Brown hydroboration....Pages 70-71 Bucherer carbazole synthesis....Pages 72-73 Bucherer reaction....Pages 74-75 Bucherer—Bergs reaction....Pages 76-77 Büchner ring expansion....Pages 78-79 Buchwald–Hartwig amination....Pages 80-83 Burgess reagent....Pages 84-86 Burke boronates....Pages 87-89 Cadiot–Chodkiewicz coupling....Pages 90-91 Camps quinoline synthesis....Pages 92-93 Cannizzaro reaction....Pages 94-95 Carroll rearrangement....Pages 96-97 Castro–Stephens coupling....Pages 98-99 Chan alkyne reduction....Pages 100-101 Chan–Lam C–X coupling reaction....Pages 102-104 Chapman rearrangement....Pages 105-106 Chichibabin pyridine synthesis....Pages 107-109 Chugaev elimination....Pages 110-111 Ciamician–Dennsted rearrangement....Pages 112-112 Claisen condensation....Pages 113-114 Claisen isoxazole synthesis....Pages 115-116 Claisen rearrangements....Pages 117-128 Clemmensen reduction....Pages 129-130 Combes quinoline synthesis....Pages 131-132 Conrad–Limpach reaction....Pages 133-134 Cope elimination reaction....Pages 135-136 Cope rearrangement....Pages 137-142 Corey–Bakshi–Shibata (CBS) reagent....Pages 143-145 Corey–Chaykovsky reaction....Pages 146-147 Corey–Fuchs reaction....Pages 148-149 Corey–Kim oxidation....Pages 150-151 Corey–Nicolaou macrolactonization....Pages 152-153 Corey–Seebach reaction....Pages 154-155 Corey–Winter olefin synthesis....Pages 156-158 Criegee glycol cleavage....Pages 159-160 Criegee mechanism of ozonolysis....Pages 161-161 Curtius rearrangement....Pages 162-164 Dakin oxidation....Pages 165-166 Dakin–West reaction....Pages 167-168 Darzens condensation....Pages 169-170 Delépine amine synthesis....Pages 171-172 de Mayo reaction....Pages 173-174 Demjanov rearrangement....Pages 175-178 Dess–Martin periodinane oxidation....Pages 179-181 Dieckmann condensation....Pages 182-183 Diels–Alder reaction....Pages 184-189 Dienone–phenol rearrangement....Pages 190-191 Di–π–methane rearrangement....Pages 192-193 Doebner quinoline synthesis....Pages 194-195 Doebner–von Miller reaction....Pages 196-197 Dötz reaction....Pages 198-199 Dowd–Beckwith ring expansion....Pages 200-201 Dudley reagent....Pages 202-203 Erlenmeyer–Plöchl azlactone synthesis....Pages 204-205 Eschenmoser’s salt....Pages 206-207 Eschenmoser–Tanabe fragmentation....Pages 208-209 Eschweiler–Clarke reductive alkylation of amines....Pages 210-211 Evans aldol reaction....Pages 212-213 Favorskii rearrangement....Pages 214-217 Feist–Bénary furan synthesis....Pages 218-219 Ferrier carbocyclization....Pages 220-221 Ferrier glycal allylic rearrangement....Pages 222-224 Fiesselmann thiophene synthesis....Pages 225-226 Fischer indole synthesis....Pages 227-228 Fischer oxazole synthesis....Pages 229-230 Fleming–Kumada oxidation....Pages 231-233 Friedel–Crafts reaction....Pages 234-237 Friedländer quinoline synthesis....Pages 238-239 Fries rearrangement....Pages 240-242 Fukuyama amine synthesis....Pages 243-244 Fukuyama reduction....Pages 245-246 Gabriel synthesis....Pages 247-249 Gabriel–Colman rearrangement....Pages 250-250 Gassman indole synthesis....Pages 251-252 Gattermann–Koch reaction....Pages 253-253 Gewald aminothiophene synthesis....Pages 254-256 Glaser coupling....Pages 257-261 Gomberg–Bachmann reaction....Pages 262-262 Gould–Jacobs reaction....Pages 263-265 Grignard reaction....Pages 266-267 Grob fragmentation....Pages 268-269 Guareschi–Thorpe condensation....Pages 270-270 Hajos–Wiechert reaction....Pages 271-272 Haller–Bauer reaction....Pages 273-273 Hantzsch dihydropyridine synthesis....Pages 274-275 Hantzsch pyrrole synthesis....Pages 276-276 Heck reaction....Pages 277-280 Hegedus indole synthesis....Pages 281-281 Hell—Volhard—Zelinsky reaction....Pages 302-303 Henry nitroaldol reaction....Pages 284-285 Hinsberg synthesis of thiophene derivatives....Pages 286-287 Hiyama cross-coupling reaction....Pages 288-289 Hofmann rearrangement....Pages 290-291 Hofmann–Löffler–Freytag reaction....Pages 292-293 Horner—Wadsworth—Emmons reaction....Pages 294-295 Houben–Hoesch reaction....Pages 296-297 Hunsdiecker–Borodin reaction....Pages 298-299 Jacobsen–Katsuki epoxidation....Pages 300-301 Japp–Klingemann hydrazone synthesis....Pages 302-303 Jones oxidation....Pages 304-308 Julia–Kocienski olefination....Pages 309-310 Julia–Lythgoe olefination....Pages 311-312 Kahne glycosidation....Pages 313-314 Knoevenagel condensation....Pages 315-316 Knorr pyrazole synthesis....Pages 317-318 Koch–Haaf carbonylation....Pages 319-319 Koenig–Knorr glycosidation....Pages 320-321 Kostanecki reaction....Pages 322-322 Kröhnke pyridine synthesis....Pages 323-324 Kumada cross-coupling reaction....Pages 325-327 Lawesson’s reagent....Pages 328-329 Leuckart–Wallach reaction....Pages 330-331 Lossen rearrangement....Pages 332-333 McFadyen–Stevens reduction....Pages 334-334 McMurry coupling....Pages 335-336 Mannich reaction....Pages 337-338 Martin’s sulfurane dehydrating reagent....Pages 339-340 Masamune–Roush conditions for the Horner–Emmons reaction....Pages 341-342 Meerwein’s salt....Pages 343-344 Meerwein–Ponndorf–Verley reduction....Pages 345-346 Meisenheimer complex....Pages 347-348 [1,2]-Meisenheimer rearrangement....Pages 349-349 [2,3]-Meisenheimer rearrangement....Pages 350-350 Meyers oxazoline method....Pages 351-352 Meyer–Schuster rearrangement....Pages 353-354 Michael addition....Pages 355-356 Michaelis–Arbuzov phosphonate synthesis....Pages 357-358 Midland reduction....Pages 359-360 Minisci reaction....Pages 361-362 Mislow–Evans rearrangement....Pages 363-364 Mitsunobu reaction....Pages 365-367 Miyaura borylation....Pages 368-369 Moffatt oxidation....Pages 370-370 Morgan–Walls reaction....Pages 371-372 Mori–Ban indole synthesis....Pages 373-374 Mukaiyama aldol reaction....Pages 375-376 Mukaiyama Michael addition....Pages 377-378 Mukaiyama reagent....Pages 379-381 Myers–Saito cyclization....Pages 382-382 Nazarov cyclization....Pages 383-384 Neber rearrangement....Pages 385-386 Nef reaction....Pages 387-388 Negishi cross-coupling reaction....Pages 389-390 Nenitzescu indole synthesis....Pages 391-392 Newman–Kwart rearrangement....Pages 393-394 Nicholas reaction....Pages 395-396 Nicolaou IBX dehydrogenation....Pages 397-398 Noyori asymmetric hydrogenation....Pages 399-400 Nozaki–Hiyama–Kishi reaction....Pages 401-402 Nysted reagent....Pages 403-403 Oppenauer oxidation....Pages 404-405 Overman rearrangement....Pages 406-407 Paal thiophene synthesis....Pages 408-408 Paal–Knorr furan synthesis....Pages 409-410 Paal–Knorr pyrrole synthesis....Pages 411-412 Parham cyclization....Pages 413-414 Passerini reaction....Pages 415-416 Paternó–Büchi reaction....Pages 417-418 Pauson–Khand reaction....Pages 419-420 Payne rearrangement....Pages 421-422 Pechmann coumarin synthesis....Pages 423-423 Perkin reaction....Pages 424-425 Petasis reaction....Pages 426-427 Petasis reagent....Pages 428-429 Peterson olefination....Pages 430-431 Pictet–Gams isoquinoline synthesis....Pages 432-433 Pictet–Spengler tetrahydroisoquinoline synthesis....Pages 1-2 Pinacol rearrangement....Pages 436-437 Pinner reaction....Pages 438-439 Polonovski reaction....Pages 440-441 Polonovski–Potier reaction....Pages 442-443 Pomeranz–Fritsch reaction....Pages 444-446 Prévost trans-dihydroxylation....Pages 447-447 Prins reaction....Pages 448-449 Pschorr cyclization....Pages 450-451 Pummerer rearrangement....Pages 452-453 Ramberg–Bäcklund reaction....Pages 454-455 Reformatsky reaction....Pages 456-457 Regitz diazo synthesis....Pages 458-459 Reimer–Tiemann reaction....Pages 460-460 Reissert reaction....Pages 461-462 Reissert indole synthesis....Pages 463-464 Ring-closing metathesis (RCM)....Pages 465-467 Ritter reaction....Pages 468-469 Robinson annulation....Pages 470-471 Robinson–Gabriel synthesis....Pages 472-473 Robinson–Schöpf reaction....Pages 474-475 Rosenmund reduction....Pages 476-477 Rubottom oxidation....Pages 478-479 Rupe rearrangement....Pages 480-481 Saegusa oxidation....Pages 482-483 Sakurai allylation reaction....Pages 484-485 Sandmeyer reaction....Pages 486-487 Schiemann reaction....Pages 1-2 Schmidt rearrangement....Pages 1-2 Schmidt’s trichloroacetimidate glycosidation reaction....Pages 492-493 Shapiro reaction....Pages 494-495 Sharpless asymmetric amino-hydroxylation....Pages 496-498 Sharpless asymmetric dihydroxylation....Pages 499-501 Sharpless asymmetric epoxidation....Pages 502-504 Sharpless olefin synthesis....Pages 505-506 Simmons–Smith reaction....Pages 507-508 Skraup quinoline synthesis....Pages 509-510 Smiles rearrangement....Pages 511-514 Sommelet reaction....Pages 515-516 Sommelet–Hauser rearrangement....Pages 517-518 Sonogashira reaction....Pages 519-520 Staudinger ketene cycloaddition....Pages 521-522 Staudinger reduction....Pages 523-524 Stetter reaction....Pages 525-526 Still–Gennari phosphonate reaction....Pages 527-528 Stille coupling....Pages 529-530 Stille–Kelly reaction....Pages 531-531 Stobbe condensation....Pages 532-533 Strecker amino acid synthesis....Pages 534-535 Suzuki–Miyaura coupling....Pages 536-537 Swern oxidation....Pages 538-539 Takai reaction....Pages 540-541 Tebbe’s reagent....Pages 542-543 TEMPO oxidation....Pages 544-545 Thorpe–Ziegler reaction....Pages 546-547 Tsuji–Trost reaction....Pages 548-550 Ugi reaction....Pages 551-553 Ullmann coupling....Pages 554-555 van Leusen oxazole synthesis....Pages 556-557 Vilsmeier– Haack reaction....Pages 558-559 Vinylcyclopropane–cyclopentene rearrangement....Pages 560-561 von Braun reaction....Pages 562-563 Wacker oxidation....Pages 564-565 Wagner–Meerwein rearrangement....Pages 566-567 Weiss–Cook reaction....Pages 568-569 Wharton reaction....Pages 570-571 White Reagent....Pages 572-575 Willgerodt–Kindler reaction....Pages 576-577 Wittig reaction....Pages 578-581 [1,2]-Wittig rearrangement....Pages 582-583 [2,3]-Wittig rearrangement....Pages 584-585 Wohl–Ziegler reaction....Pages 586-587 Wolff rearrangement....Pages 588-589 Wolff–Kishner reduction....Pages 590-591 Woodward cis-dihydroxylation....Pages 592-593 Yamaguchi esterification....Pages 594-595 Zincke reaction....Pages 596-598 Back Matter....Pages 1-23 I don't have my name on anything that I don't really do. –Heidi Klum Can the organic chemists associated with so-called “Named Reactions” make the same claim as supermodel Heidi Klum? Many scholars of chemistry do not hesitate to point out that the names associated with “name reactions” are often not the actual inventors. For instance, the Arndt–Eistert reaction has nothing to do with either Arndt or Eistert, Pummerer did not discover the “Pummerer” rearrangement, and even the famous Birch reduction owes its initial discovery to someone named Charles Wooster (first reported in a DuPont patent). The list goes on and on... But does that mean we should ignore, boycott, or outlaw “named reactions”? Absolutely not. The above examples are merely exceptions to the rule. In fact, the chemists associated with name reactions are typically the original discoverers, contribute greatly to its general use, and/or are the first to popularize the transformation. Regardless of the controversial history underlying certain named reactions, it is the students of organic chemistry who benefit the most from the cataloging of reactions by name. Indeed, it is with education in mind that Dr. Jack Li has masterfully brought the chemical community the latest edition of Name Reactions. "The fourth edition contains major improvements over the previous edition. In addition to updated references, each reaction is now supplemented with two to three representative examples in synthesis to showcase its synthetic utility. Biographical sketches for the chemists who discovered or developed those name reactions have been included. Furthermore, the subject index is significantly expanded." "Different from other books on name reactions in organic chemistry, Name Reactions: A Collection of Detailed Reaction Mechanisms focuses on their mechanisms. It covers over 300 classical as well as contemporary name reactions. Each reaction is delineated by its detailed step-by-step, electron-pushing mechanism, supplemented with the original and the latest references, especially review articles. Thus, it is not only an indispensable resource for senior undergraduate and graduate students for learning and exams, but also a good reference book for all chemists interested in name reactions."--Jacket