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.
Table of Contents:
1. Abnormal Claisen rearrangement.- 2. Alder ene reaction.- 3. Aldol condensation.- 4. Allan—Robinson reaction.- 5. Alper carbonylation.- 6. Amadori rearrangement.- 7. Angeli—Rimini hydroxamic acid synthesis.- 8. ANRORC mechanism.- 9. Arndt—Eistert homologation.- 10. Auwers reaction.- 11. Baeyer—Drewson indigo synthesis.- 12. Baeyer—Villiger oxidation.- 13. Baker—Venkataraman rearrangement.- 14. Bamberger rearrangement.- 15. Bamford—Stevens reaction.- 16. Bargellini reaction.- 17. Bartoli indole synthesis.- 18. Barton decarboxylation.- 19. Barton—McCombie deoxygenation.- 20. Barton nitrite photolysis.- 21. Baylis—Hillman reaction.- 22. Beckmann rearrangement.- 23. Beirut reaction.- 24. Benzilic acid rearrangement.- 25. Benzoin condensation.- 26. Bergman cyclization.- 27. Biginelli pyrimidone synthesis.- 28. Birch reduction.- 29. Bischler—Möhlau indole synthesis.- 30. Bischler—Napieralski reaction.- 31. Blaise reaction.- 32. Blanc chloromethylation reaction.- 33. Boekelheide reaction.- 34. Boger pyridine synthesis.- 35. Boord reaction.- 36. Borsche—Drechsel cyclization.- 37. Boulton—Katritzky rearrangement.- 38. Bouveault aldehyde synthesis.- 39. Bouveault—Blanc reduction.- 40. Boyland—Sims oxidation.- 41. Bradsher reaction.- 42. Brook rearrangement.- 43. Brown hydroboration reaction.- 44. Bucherer carbazole synthesis.- 45. Bucherer reaction.- 46. Bucherer—Bergs reaction.- 47. Buchner—Curtius—Schlotterbeck reaction.- 48. Buchner method of ring expansion.- 49. Buchwald—Hartwig C—N bond and C—O bond formation reactions.- 50. Burgess dehydrating reagent.- 51. Cadiot—Chodkiewicz coupling.- 52. Cannizzaro dispropotionation reaction.- 53. Carroll rearrangement.- 54. Castro—Stephens coupling.- 55. Chapman rearrangement.- 56. Chichibabin amination reaction.- 57. Chichibabin pyridine synthesis.- 58. Chugaev reaction.- 59. Ciamician—Dennsted rearrangement.- 60. Claisen condensation.- 61. Claisen rearrangement.- 62. Clarke—Eschweiler reductive alkylation of amines.- 63. Clemmensen reduction.- 64. Combes quinoline synthesis.- 65. Conrad—Limpach reaction.- 66. Cook—Heilbron thiazole synthesis.- 67. Cope elimination reaction.- 68. Cope, oxy-Cope, and anionic oxy-Cope rearrangements.- 69. Corey—Bakshi—Shibata (CBS) reduction.- 70. Corey—Chaykovsky reaction.- 71. Corey—Fuchs reaction.- 72. Corey—Kim oxidation.- 73. Corey—Winter olefin synthesis.- 74. Cornforth rearrangement.- 75. Criegee glycol cleavage.- 76. Criegee mechanism of ozonolysis.- 77. Curtius rearrangement.- 78. Dakin oxidation.- 79. Dakin—West reaction.- 80. Danheiser annulation.- 81. Darzens glycidic ester condensation.- 82. Davis chiral oxaziridine reagent.- 83. de Mayo reaction.- 84. Demjanov rearrangement.- 85. Dess—Martin periodinane oxidation.- 86. Dieckmann condensation.- 87. Diels—Alder reaction.- 88. Dienone—phenol rearrangement.- 89. Di-?-methane rearrangement.- 90. Doebner reaction.- 91. Doebner—von Miller reaction.- 92. Doering—LaFlamme allene synthesis.- 93. Dornow—Wiehler isoxazole synthesis.- 94. Dötz reaction.- 95. Dowd ring expansion.- 96. Dutt—Wormall reaction.- 97. Eglinton reaction.- 98. Eschenmoser coupling reaction.- 99. Eschenmoser—Tanabe fragmentation.- 100. Etard reaction.- 101. Evans aldol reaction.- 102. Favorskii rearrangement and Quasi-Favorskii rearrangement.- 103. Feist—Bénary furan synthesis.- 104. Ferrier rearrangement.- 105. Finkelstein reaction.- 106. Fischer—Hepp rearrangement.- 107. Fischer indole synthesis.- 108. Fischer—Speier esterification.- 109. Fleming oxidation.- 110. Forster reaction.- 111. Frater—Seebach alkylation.- 112. Friedel—Crafts reaction.- 113. Friedländer synthesis.- 114. Fries rearrangement.- 115. Fritsch—Buttenberg—Wiechell rearrangement.- 116. Fujimoto—Belleau reaction.- 117. Fukuyama amine synthesis.- 118. Gabriel synthesis.- 119. Gassman indole synthesis.- 120. Gattermann—Koch reaction.- 121. Gewald aminothiophene synthesis.- 122. Glaser coupling.- 123. Gomberg—Bachmann reaction.- 124. Gribble indole reduction.- 125. Gribble reduction of diaryl ketones.- 126. Grignard reaction.- 127. Grob fragmentation.- 128. Guareschi—Thorpe condensation.- 129. Hajos—Wiechert reaction.- 130. Haller—Bauer reaction.- 131. Hantzsch pyridine synthesis.- 132. Hantzsch pyrrole synthesis.- 133. Haworth reaction.- 134. Hayashi rearrangement.- 135. Heck reaction.- 136. Hegedus indole synthesis.- 137. Hell—Volhardt—Zelinsky reaction.- 138. Henry reaction (nitroaldol reaction).- 139. Herz reaction.- 140. Heteroaryl Heck reaction.- 141. Hiyama cross-coupling reaction.- 142. Hoch—Campbell aziridine synthesis.- 143. Hodges—Vedejs metallation of oxazoles.- 144. Hofmann rearrangement (Hofmann degradation reaction).- 145. Hofmann—Löffler—Freytag reaction.- 146. Hofmann—Martius reaction (Reilly—Hickinbottom rearrangement).- 147. Hooker oxidation.- 148. Horner—Wadsworth—Emmons reaction.- 149. Houben—Hoesch synthesis.- 150. Hunsdiecker reaction.- 151. Ing—Manske procedure.- 152. Jacobsen—Katsuki epoxidation.- 153. Jacobsen rearrangement.- 154. Japp—Klingemann hydrazone synthesis.- 155. Julia—Lythgoe olefination.- 156. Kahne glycosidation.- 157. Keck stereoselective allylation.- 158. Keck macrolactonization.- 159. Kemp elimination.- 160. Kennedy oxidative cyclization.- 161. Kharasch addition reaction.- 162. Knöevenagel condensation.- 163. Knorr pyrrole synthesis.- 164. Koch carbonylation reaction (Koch—Haaf carbonylation reaction).- 165. Koenig—Knorr glycosidation.- 166. Kolbe electrolytic coupling.- 167. Kolbe—Schmitt reaction.- 168. Kostanecki reaction.- 169. Krapcho decarboxylation.- 170. Kröhnke reaction (pyridine synthesis).- 171. Kumada cross-coupling reaction.- 172. Larock indole synthesis.- 173. Lawesson’s reagent.- 174. Leuckart—Wallach reaction.- 175. Lieben haloform reaction.- 176. Liebeskind—Srogl coupling.- 177. Lossen rearrangement.- 178. Luche reduction.- 179. McFadyen—Stevens reduction.- 180. McLafferty rearrangement.- 181. McMurry coupling.- 182. Madelung indole synthesis.- 183. Mannich reaction.- 184. Marshall boronate fragmentation.- 185. Martin’s sulfurane dehydrating reagent.- 186. Masamune—Roush conditions.- 187. Meerwein arylation.- 188. Meerwein—Ponndorf—Verley reduction.- 189. Meinwald rearrangement.- 190. Meisenheimer complex.- 191. Meisenheimer rearrangement.- 192. Meyer—Schuster rearrangement.- 193. Michael addition.- 194. Michaelis—Arbuzov phosphonate synthesis.- 195. Midland reduction.- 196. Miller—Loudon—Snyder nitrile synthesis.- 197. Mislow—Evans rearrangement.- 198. Mitsunobu reaction.- 199. Miyaura boration reaction.- 200. Moffatt oxidation.- 201. Morgan—Walls reaction (Pictet—Hubert reaction).- 202. Mori—Ban indole synthesis.- 203. Morin rearrangement.- 204. Mukaiyama aldol reaction.- 205. Mukaiyama esterification.- 206. Myers—Saito cyclization.- 207. Nametkin rearrangement (retropinacol rearrangement).- 208. Nazarov cyclization.- 209. Neber rearrangement.- 210. Nef reaction.- 211. Negishi cross-coupling reaction.- 212. Nenitzescu indole synthesis.- 213. Nicholas reaction.- 214. Noyori asymmetric hydrogenation.- 215. Nozaki—Hiyama—Kishi reaction.- 216. Oppenauer oxidation.- 217. Orton rearrangement.- 218. Overman rearrangement.- 219. Paal—Knorr furan synthesis.- 220. Paal—Knorr pyrrole synthesis.- 221. Parham cyclization.- 222. Passerini reaction.- 223. Paterno—Büchi reaction.- 224. Pauson—Khand cyclopentenone synthesis.- 225. Payne rearrangement.- 226. Pechmann condensation (coumarin synthesis).- 227. Pechmann pyrazole synthesis.- 228. Perkin reaction (cinnamic acid synthesis).- 229. Perkow vinyl phosphate synthesis.- 230. Peterson olefination.- 231. Pfau—Plattner azulene synthesis.- 232. Pfitzinger quinoline synthesis.- 233. Pictet—Gams isoquinoline synthesis.- 234. Pictet—Spengler tetrahydroisoquinoline synthesis.- 235. Pinacol rearrangement.- 236. Pinner synthesis.- 237. Polonovski reaction.- 238. Polonovski—Potier rearrangement.- 239. Pomeranz—Fritsch reaction.- 240. Prévost trans-dihydroxylation.- 241. Prilezhaev reaction.- 242. Prins reaction.- 243. Pschorr ring closure.- 244. Pummerer rearrangement.- 245. Ramberg—Bäcklund olefin synthesis.- 246. Reformatsky reaction.- 247. Regitz diazo synthesis.- 248. Reimer—Tiemann reaction.- 249. Reissert reaction (aldehyde synthesis).- 250. Riley oxidation (selenium dioxide oxidation).- 251. Ring-closing metathesis (RCM) using Grubbs and Schrock catalysts.- 252. Ritter reaction.- 253. Robinson annulation.- 254. Robinson—Schöpf reaction.- 255. Rosenmund reduction.- 256. Roush allylboronate reagent.- 257. Rubottom oxidation.- 258. Rupe rearrangement.- 259. Rychnovsky polyol synthesis.- 260. Sakurai allylation reaction (Hosomi—Sakurai reaction).- 261. Sandmeyer reaction.- 262. Sarett oxidation.- 263. Schiemann reaction (Balz—Schiemann reaction).- 264. Schlosser modification of the Wittig reaction.- 265. Schmidt reaction.- 266. Schmidt’s trichloroacetimidate glycosidation reaction.- 267. Scholl reaction.- 268. Schöpf reaction.- 269. Schotten—Baumann reaction.- 270. Shapiro reaction.- 271. Sharpless asymmetric amino hydroxylation.- 272. Sharpless asymmetric epoxidation.- 273. Sharpless dihydroxylation.- 274. Shi asymmetric epoxidation.- 275. Simmons—Smith reaction.- 276. Simonini reaction.- 277. Simonis chromone cyclization.- 278. Skraup quinoline synthesis.- 279. Smiles rearrangement.- 280. Sommelet reaction.- 281. Sommelet—Hauser (ammonium ylide) rearrangement.- 282. Sonogashira reaction.- 283. Staudinger reaction.- 284. Stetter reaction (Michael—Stetter reaction).- 285. Stevens rearrangement.- 286. Stieglitz rearrangement.- 287. Still—Gennari phosphonate reaction.- 288. Stille coupling.- 289. Stille—Kelly reaction.- 290. Stobbe condensation.- 291. Stollé synthesis.- 292. Stork enamine reaction.- 293. Strecker amino acid synthesis.- 294. Suzuki coupling.- 295. Swern oxidation.- 296. Tamao—Kumada oxidation.- 297. Tebbe olefination (Petasis alkenylation).- 298. Thorpe—Ziegler reaction.- 299. Tiemann rearrangement.- 300. Tiffeneau—Demjanov rearrangement.- 301. Tishchenko reaction.- 302. Tollens reaction.- 303. Tsuji—Trost allylation.- 304. Ueno—Stork cyclization.- 305. Ugi reaction.- 306. Ullmann reaction.- 307. Vilsmeier—Haack reaction.- 308. von Braun reaction.- 309. von Richter reaction.- 310. Wacker oxidation.- 311. Wagner—Meerwein rearrangement.- 312. Wallach rearrangement.- 313. Weinreb amide.- 314. Weiss reaction.- 315. Wenker aziridine synthesis.- 316. Wharton oxygen transposition reaction.- 317. Willgerodt—Kindler reaction.- 318. Williamson ether synthesis.- 319. Wittig reaction.- 320. [1,2]-Wittig rearrangement.- 321. [2,3]-Wittig rearrangement.- 322. Wohl—Ziegler reaction.- 323. Wolff rearrangement.- 324. Wolff—Kishner reduction.- 325. Woodward cis-dihydroxylation.- 326. Wurtz reaction.- 327. Yamada coupling reagent.- 328. Yamaguchi esterification.- 329. Zaitsev elimination.- 330. Zincke reaction.- 331. Zinin benzidine rearrangement (semidine rearrangement).
Review :
from S.R. Waldvogel, Adv. Synth. Catal. 2004, 346, 91:
"Since the second edition has increased tremendously in quality, it is highly recommended to all synthetically oriented chemists as compulsory reading. With a relativele comprehensive collection of modern named reactions, including more recent discoveries that are not found in standard works, this book surpasses previous monographs on this topic and should find its way into every good scientific library."
The best books are very reader friendly and this publication is heading in that direction. Organic chemistry researchers, students and teachers will make good use of this book.
Helmut Huegel, FRACI, RMIT University
Chemistry in Australia, Magazine of the Royal Australian Chemical Institute, April 2004
From the reviews of the third edition:
"Like its predecessors, this edition of Name Reactions covers over 300 classical and contemporary name reactions, with each entry including the name of the reaction, a short description of it, the step-by-step mechanism, and a list of references. Improvements to this edition include updated references, two to three examples of applications of the featured reaction … brief biographical sketches of the discoverers and developers of the reaction in question, and an expanded subject index." (JACS, Vol. 129 (2), 2007)
"Name Reactions … has been expanded significantly as compared to the Second Edition. The book contains a multitude of new name reactions and, as a new feature, reaction examples from the current literature. Each name reaction is illustrated with a reaction scheme, an accurate and detailed mechanism, and two interesting examples from current work. In addition, numerous up-to-date citations are provided that can facilitate an initial literature search. … `Name Reactions’ is an especially useful book for obtaining a first introduction to a multitude of important and also current name reactions. Moreover, the mechanistic explanations in the form of excellent schemes provide a basis for advanced students to practice these mechanisms. A number of errors from the Second Edition have been corrected, and this fact together with the successful enhancements make a good case for purchasing this latest edition." (www.organic.chemistry.org, March, 2007)
