Name Reactions : A Collection of Detailed Reaction Mechanisms

The second edition includes five points of improvement: (a) Additional 16 name reactions have been supplemented; (b) I have corrected typos and a few dubious mechanisms in the first edition. I wish to thank Prof. Rick L. Danheiser of Massa­ chusetts Institute of Technology and Mr. Yiqian Lian of Michigan State Univer­ sity for invaluable comments and suggestions. I have also incurred many debts of gratitude to Prof. Brian. M. Stoltz of California Institute of Technology and his students, Eric Ashley, Doug Behenna, Dan Caspi, Neil Garg, Blake Greene, Jeremy May, Sarah Spessard, Uttam Tambar, Raissa Trend, and Ryan Zeidan for proofreading the final draft of the second edition; (c) The references are expanded and updated; (d) A more thorough index has been implemented so the reader may navigate through the book more easily; (e) The short descriptions of name reactions given as mnemonics seem to be helpful to both novices and veterans. As a result, I added the descriptions for most reactions. Finally, I am grateful for permission to use the postage stamps on the inner covers from respective postal authorities, who still retail the copyrights of those stamps. Jack Li Ann Arbor, Michigan, May 2003 Preface to the first edition What's in a name? That which we call a rose by any other name would smell as 1 sweet. Front Matter....Pages I-XVIII Abnormal Claisen rearrangement....Pages 1-1 Alder ene reaction....Pages 2-2 Aldol condensation....Pages 3-3 Allan-Robinson reaction....Pages 4-5 Alper carbonylation....Pages 6-7 Amadori rearrangement....Pages 8-8 Angeli-Rimini hydroxamic acid synthesis....Pages 9-9 ANRORC mechanism....Pages 10-10 Arndt-Eistert homologation....Pages 11-12 Auwers reaction....Pages 13-13 Baeyer-Drewson indigo synthesis....Pages 14-15 Baeyer-Villiger oxidation....Pages 16-16 Baker-Venkataraman rearrangement....Pages 17-17 Bamberger rearrangement....Pages 18-18 Bamford-Stevens reaction....Pages 19-19 Bargellini reaction....Pages 20-20 Bartoli indole synthesis....Pages 21-21 Barton decarboxylation....Pages 22-22 Barton-McCombie deoxygenation....Pages 23-23 Barton nitrite photolysis....Pages 24-25 Baylis-Hillman reaction....Pages 26-27 Beckmann rearrangement....Pages 28-28 Beirut reaction....Pages 29-30 Benzilic acid rearrangement....Pages 31-31 Benzoin condensation....Pages 32-32 Bergman cyclization....Pages 33-33 Biginelli pyrimidone synthesis....Pages 34-35 Birch reduction....Pages 36-37 Bischler-Möhlau indole synthesis....Pages 38-38 Bischler-Napieralski reaction....Pages 39-39 Blaise reaction....Pages 40-40 Blanc chloromethylation reaction....Pages 41-41 Boekelheide reaction....Pages 42-42 Boger pyridine synthesis....Pages 43-43 Boord reaction....Pages 44-44 Borsche-Drechsel cyclization....Pages 45-45 Boulton-Katritzky rearrangement....Pages 46-46 Bouveault aldehyde synthesis....Pages 47-47 Bouveault-Blanc reduction....Pages 48-48 Boyland-Sims oxidation....Pages 49-50 Bradsher reaction....Pages 51-51 Brook rearrangement....Pages 52-52 Brown hydroboration reaction....Pages 53-53 Bucherer carbazole synthesis....Pages 54-55 Bucherer reaction....Pages 56-56 Bucherer-Bergs reaction....Pages 57-57 Buchner-Curtius-Schlotterbeck reaction....Pages 58-58 Buchner method of ring expansion....Pages 59-59 Buchwald-Hartwig C-N bond and C-O bond formation reactions....Pages 60-60 Burgess dehydrating reagent....Pages 61-61 Cadiot-Chodkiewicz coupling....Pages 62-62 Cannizzaro disproportionation reaction....Pages 63-64 Carroll rearrangement....Pages 65-65 Castro-Stephens coupling....Pages 66-66 Chapman rearrangement....Pages 67-67 Chichibabin amination reaction....Pages 68-68 Chichibabin pyridine synthesis....Pages 69-70 Chugaev elimination....Pages 71-71 Ciamician-Dennsted rearrangement....Pages 72-72 Claisen condensation....Pages 73-73 Claisen, Eschenmoser-Claisen, Johnson-Claisen, and Ireland-Claisen rearrangements....Pages 74-75 Clarke-Eschweiler reductive alkylation of amines....Pages 76-76 Clemmensen reduction....Pages 77-78 Combes quinoline synthesis....Pages 79-80 Conrad-Limpach reaction....Pages 81-81 Cook-Heilbron thiazole synthesis....Pages 82-82 Cope elimination reaction....Pages 83-83 Cope, oxy-Cope, and anionic oxy-Cope rearrangements....Pages 84-85 Corey-Bakshi-Shibata (CBS) reduction....Pages 86-87 Corey-Chaykovsky reaction....Pages 88-89 Corey-Fuchs reaction....Pages 90-91 Corey-Kim oxidation....Pages 92-92 Corey-Winter olefin synthesis....Pages 93-94 Cornforth rearrangement....Pages 95-95 Criegee glycol cleavage....Pages 96-96 Criegee mechanism of ozonolysis....Pages 97-97 Curtius rearrangement....Pages 98-98 Dakin oxidation....Pages 99-99 Dakin-West reaction....Pages 100-101 Danheiser annulation....Pages 102-102 Darzens glycidic ester condensation....Pages 103-103 Davis chiral oxaziridine reagents....Pages 104-104 De Mayo reaction....Pages 105-106 Demjanov rearrangement....Pages 107-108 Dess-martin periodinane oxidation....Pages 109-109 Dieckmann condensation....Pages 110-110 Diels-Alder reaction....Pages 111-112 Dienone-phenol rearrangement....Pages 113-113 Di- π -methane rearrangement....Pages 114-114 Doebner reaction....Pages 115-116 Doebner–von Miller reaction....Pages 117-118 Doering–LaFlamme allene synthesis....Pages 119-119 Dornow–Wiehler isoxazole synthesis....Pages 120-121 Dötz reaction....Pages 122-122 Dowd ring expansion....Pages 123-124 Dutt-wormall reaction....Pages 125-125 Eglinton reaction....Pages 126-126 Eschenmoser coupling reaction....Pages 127-127 Eschenmoser-Tanabe fragmentation....Pages 128-128 Étard reaction....Pages 129-129 Evans aldol reaction....Pages 130-131 Favorskii rearrangement and Quasi-Favorskii rearrangement....Pages 132-133 Feist-Bénary furan synthesis....Pages 134-134 Ferrier rearrangement....Pages 135-135 Finkelstein reaction....Pages 136-136 Fischer-Hepp rearrangement....Pages 137-137 Fischer indole synthesis....Pages 138-138 Fischer-Speier esterification....Pages 139-139 Fleming oxidation....Pages 140-141 Forster reaction....Pages 142-143 Frater-Seebach alkylation....Pages 144-144 Friedel-Crafts reaction....Pages 145-146 Friedländer synthesis....Pages 147-148 Fries rearrangement....Pages 149-150 Fritsch-Buttenberg-Wiechell rearrangement....Pages 151-151 Fujimoto-Belleau reaction....Pages 152-152 Fukuyama amine synthesis....Pages 153-154 Gabriel synthesis....Pages 155-155 Gassman indole synthesis....Pages 156-156 Gattermann-Koch reaction....Pages 157-157 Gewald aminothiophene synthesis....Pages 158-159 Glaser coupling....Pages 160-160 Gomberg-Bachmann reaction....Pages 161-161 Gribble indole reduction....Pages 162-162 Gribble reduction of diaryl ketones....Pages 163-163 Grignard reaction....Pages 164-165 Grob fragmentation....Pages 166-167 Guareschi-Thorpe condensation....Pages 168-168 Hajos-Wiechert reaction....Pages 169-170 Haller-Bauer reaction....Pages 171-171 Hantzsch pyridine synthesis....Pages 172-173 Hantzsch pyrrole synthesis....Pages 174-174 Haworth reaction....Pages 175-176 Hayashi rearrangement....Pages 177-178 Heck reaction....Pages 179-180 Hegedus indole synthesis....Pages 181-181 Hell-Volhardt-Zelinsky reaction....Pages 182-182 Henry reaction (nitroaldol reaction)....Pages 183-183 Herz reaction....Pages 184-185 Heteroaryl Heck reaction....Pages 186-186 Hiyama cross-coupling reaction....Pages 187-188 Hoch-Campbell aziridine synthesis....Pages 189-190 Hodges-Vedejs metallation of oxazoles....Pages 191-191 Hofmann rearrangement (Hofmann degradation reaction)....Pages 192-192 Hofmann-Löffler-Freytag reaction....Pages 193-193 Hofmann-Martius reaction....Pages 194-195 Hooker oxidation....Pages 196-197 Horner-Wadsworth-Emmons reaction....Pages 198-199 Houben-Hoesch reaction....Pages 200-201 Hunsdiecker reaction....Pages 202-202 Ing-Manske procedure....Pages 203-203 Jacobsen-Katsuki epoxidation....Pages 204-205 Jacobsen rearrangement....Pages 206-207 Japp-Klingemann hydrazone synthesis....Pages 208-208 Julia-Lythgoe olefination....Pages 209-210 Kahne glycosidation....Pages 211-212 Keck stereoselective allylation....Pages 213-214 Keck macrolactonization....Pages 215-216 Kemp elimination....Pages 217-217 Kennedy oxidative cyclization....Pages 218-218 Kharasch addition reaction....Pages 219-219 Knöevenagel condensation....Pages 220-221 Knorr pyrrole synthesis....Pages 222-222 Koch carbonylation reaction (Koch-Haaf carbonylation reaction)....Pages 223-224 Koenig-Knorr glycosidation....Pages 225-225 Kolbe electrolytic coupling....Pages 226-226 Kolbe-Schmitt reaction....Pages 227-227 Kostanecki reaction....Pages 228-229 Krapcho decarboxylation....Pages 230-230 Kröhnke reaction (pyridine synthesis)....Pages 231-232 Kumada cross-coupling reaction....Pages 233-234 Larock indole synthesis....Pages 235-235 Lawesson’s reagent....Pages 236-236 Leuckart-Wallach reaction....Pages 237-237 Lieben haloform reaction....Pages 238-238 Liebeskind-Srogl coupling....Pages 239-239 Lossen rearrangement....Pages 240-240 Luche reduction....Pages 241-241 McFadyen-Stevens reduction....Pages 242-242 McLafferty fragmentation....Pages 243-243 McMurry coupling....Pages 244-244 Madelung indole synthesis....Pages 245-245 Mannich reaction....Pages 246-247 Marshall boronate fragmentation....Pages 248-248 Martin’s sulfurane dehydrating reagent....Pages 249-250 Masamune-Roush conditions....Pages 251-252 Meerwein arylation....Pages 253-253 Meerwein-Ponndorf-Verley reduction....Pages 254-254 Meinwald rearrangement....Pages 255-255 Meisenheimer complex....Pages 256-257 Meisenheimer rearrangement....Pages 258-258 Meyer-Schuster rearrangement....Pages 259-259 Michael addition....Pages 260-260 Michaelis-Arbuzov phosphonate synthesis....Pages 261-261 Midland reduction....Pages 262-262 Miller-Loudon-Snyder nitrile synthesis....Pages 263-263 Mislow-Evans rearrangement....Pages 264-264 Mitsunobu reaction....Pages 265-265 Miyaura boration reaction....Pages 266-266 Moffatt oxidation....Pages 267-268 Morgan-Walls reaction (Pictet-Hubert reaction)....Pages 269-269 Mori-Ban indole synthesis....Pages 270-271 Morin rearrangement....Pages 272-273 Mukaiyama aldol reaction....Pages 274-274 Mukaiyama esterification....Pages 275-276 Myers-Saito cyclization....Pages 277-278 Nametkin rearrangement (Retropinacol rearrangement)....Pages 279-279 Nazarov cyclization....Pages 280-280 Neber rearrangement....Pages 281-281 Nef reaction....Pages 282-282 Negishi cross-coupling reaction....Pages 283-283 Nenitzescu indole synthesis....Pages 284-285 Nicholas reaction....Pages 286-286 Noyori asymmetric hydrogenation....Pages 287-288 Nozaki-Hiyama-Kishi reaction....Pages 289-289 Oppenauer oxidation....Pages 290-290 Orton rearrangement....Pages 291-292 Overman rearrangement....Pages 293-293 Paal-Knorr furan synthesis....Pages 294-294 Paal-Knorr pyrrole synthesis....Pages 295-295 Parham cyclization....Pages 296-297 Passerini reaction....Pages 298-298 Paterno-Büchi reaction....Pages 299-299 Pauson-Khand cyclopentenone synthesis....Pages 300-301 Payne rearrangement....Pages 302-302 Pechmann condensation (coumarin synthesis)....Pages 303-303 Pechmann pyrazole synthesis....Pages 304-304 Perkin reaction (cinnamic acid synthesis)....Pages 305-306 Perkow vinyl phosphate synthesis....Pages 307-307 Peterson olefination....Pages 308-309 Pfau-Plattner azulene synthesis....Pages 310-310 Pfitzinger quinoline synthesis....Pages 311-311 Pictet-Gams isoquinoline synthesis....Pages 312-313 Pictet-Spengler tetrahydroisoquinoline synthesis....Pages 314-314 Pinacol rearrangement....Pages 315-315 Pinner synthesis....Pages 316-316 Polonovski reaction....Pages 317-318 Polonovski-Potier reaction....Pages 319-319 Pomeranz-Fritsch reaction....Pages 320-321 Prévost trans -dihydroxylation....Pages 322-322 Prilezhaev reaction....Pages 323-323 Prins reaction....Pages 324-324 Pschorr ring closure....Pages 325-326 Pummerer rearrangement....Pages 327-327 Ramberg—Bäcklund olefin synthesis....Pages 328-328 Reformatsky reaction....Pages 329-329 Regitz diazo synthesis....Pages 330-331 Reimer-Tiemann reaction....Pages 332-333 Reissert reaction (aldehyde synthesis)....Pages 334-335 Riley oxidation (selenium dioxide oxidation)....Pages 336-336 Ring-closing metathesis (RCM) using Grubbs and Schrock catalysts....Pages 337-338 Ritter reaction....Pages 339-339 Robinson annulation....Pages 340-340 Robinson-Schöpf reaction....Pages 341-342 Rosenmund reduction....Pages 343-343 Roush allylboronate reagent....Pages 344-344 Rubottom oxidation....Pages 345-345 Rupe rearrangement....Pages 346-346 Rychnovsky polyol synthesis....Pages 347-348 Sakurai allylation reaction (Hosomi-Sakurai reaction)....Pages 349-350 Sandmeyer reaction....Pages 351-351 Sarett oxidation....Pages 352-353 Schiemann reaction (Balz-Schiemann reaction)....Pages 354-354 Schlosser modification of the Wittig reaction....Pages 355-355 Schmidt reaction....Pages 356-356 Schmidt’s trichloroacetimidate glycosidation reaction....Pages 357-358 Scholl reaction....Pages 359-360 Schöpf reaction....Pages 361-361 Schotten-Baumann reaction....Pages 362-362 Shapiro reaction....Pages 363-363 Sharpless asymmetric amino hydroxylation....Pages 364-365 Sharpless asymmetric epoxidation....Pages 366-368 Sharpless dihydroxylation....Pages 369-371 Shi asymmetric epoxidation....Pages 372-373 Simmons-Smith reaction....Pages 374-374 Simonini reaction....Pages 375-375 Simonis chromone cyclization....Pages 376-377 Skraup quinoline synthesis....Pages 378-379 Smiles rearrangement....Pages 380-380 Sommelet reaction....Pages 381-382 Sommelet-Hauser (ammonium ylide) rearrangement....Pages 383-383 Sonogashira reaction....Pages 384-385 Staudinger reaction....Pages 386-386 Stetter reaction (Michael-Stetter reaction)....Pages 387-388 Stevens rearrangement....Pages 389-390 Stieglitz rearrangement....Pages 391-391 Still-gennari phosphonate reaction....Pages 392-392 Stille coupling....Pages 393-393 Stille-kelly reaction....Pages 394-395 Stobbe condensation....Pages 396-396 Stollé synthesis....Pages 397-397 Stork enamine reaction....Pages 398-398 Strecker amino acid synthesis....Pages 399-400 Suzuki coupling....Pages 401-401 Swern oxidation....Pages 402-403 Tamao-Kumada oxidation....Pages 404-404 Tebbe olefination (Petasis alkenylation)....Pages 405-406 Thorpe-Ziegler reaction....Pages 407-407 Tiemann rearrangement....Pages 408-408 Tiffeneau-Demjanov Rearrangement....Pages 409-410 Tishchenko reaction....Pages 411-411 Tollens reaction....Pages 412-413 Tsuji-Trost reaction....Pages 414-414 Ueno-Stork cyclization....Pages 415-415 Ugi reaction....Pages 416-417 Ullmann reaction....Pages 418-418 Vilsmeier—Haack reaction....Pages 419-420 von Braun reaction....Pages 421-421 Von Richter reaction....Pages 422-423 Wacker oxidation....Pages 424-425 Wagner-Meerwein rearrangement....Pages 426-426 Wallach rearrangement....Pages 427-427 Weinreb amide....Pages 428-428 Weiss reaction....Pages 429-430 Wenker aziridine synthesis....Pages 431-431 Wharton oxygen transposition reaction....Pages 432-432 Willgerodt-Kindler reaction....Pages 433-436 Williamson ether synthesis....Pages 437-437 Wittig reaction....Pages 438-438 [1,2]-Wittig rearrangement....Pages 439-439 [2,3]-Wittig rearrangement....Pages 440-440 Wohl-Ziegler reaction....Pages 441-442 Wolff rearrangement....Pages 443-443 Wolff-Kishner reduction....Pages 444-444 Woodward cis -dihydroxylation....Pages 445-445 Wurtz reaction....Pages 446-446 Yamada coupling reagent....Pages 447-447 Yamaguchi esterification....Pages 448-449 Zaitsev elimination....Pages 450-450 Zincke reaction....Pages 451-452 Zinin benzidine rearrangement (semidine rearrangement)....Pages 453-454 Back Matter....Pages 455-465 The second edition includes: 16 additional name reactions; the references are updated and expanded; a better index; short descriptions for most of the name reactions are added; typographical and structural errors are corrected. 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 their learning and exams, but also a good reference book for all chemists interested in name reactions This book differs from others on name reactions in organic chemistry by focusing on their mechanisms. It covers over 300 classical as well as contemporary name reactions. Biographical sketches for the chemists who discovered or developed those name reactions have been included. Each reaction is delineated by its detailed step-by-step, electron-pushing mechanism, supplemented with the original and the latest references, especially review articles. This book contains major improvements over the previous edition and the subject index is significantly expanded.