Fritsch–Buttenberg–Wiechell重排反应

Fritsch–Buttenberg–Wiechell重排反应(Fritsch–Buttenberg–Wiechell rearrangement),以 Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, Heinrich G. Wiechell 的名字命名。

1,1-二芳基-2-溴代烯烃强碱(如醇盐)作用下重排为1,2-二芳基[1][2][3] [4]


Fritsch-Buttenberg-Wiechell重排
Fritsch-Buttenberg-Wiechell重排

某些烷基取代的烯烃也可发生重排。[5]

反应机理

强碱夺取烯碳上的氢,生成的碳负离子再发生α-消除生成乙烯基卡宾。最后发生1,2-芳基迁移,得到产物。

应用

利用此反应合成多炔[6]炔化物中间体被亲电试剂碘甲烷捕获。产物为鬼针草中存在的天然产物)


Fritsch-Buttenberg-Wiechell重排的应用
Fritsch-Buttenberg-Wiechell重排的应用

参见

参考资料

  1. Paul Fritsch. . Justus Liebig's Annalen der Chemie. 1894, 279 (3): 319–323. doi:10.1002/jlac.18942790310.
  2. Buttenberg, W. P. . Justus Liebig's Annalen der Chemie. 1894, 279 (3): 324–337. doi:10.1002/jlac.18942790311.
  3. Wiechell, H. . Justus Liebig's Annalen der Chemie. 1894, 279 (3): 337–344. doi:10.1002/jlac.18942790312.
  4. Köbrich, G. . Angewandte Chemie International Edition. 1965, 4: 49–68. doi:10.1002/anie.196500491.
  5. Rezaei, H.; Yamanoi, S.; Chemla, F.; Normant, J. F. . Org. Lett. 2000, 2 (4): 419–421. doi:10.1021/ol991117z.
  6. One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch-Buttenberg-Wiechell Rearrangement Thanh Luu, Yasuhiro Morisaki, Nina Cunningham, and Rik R. Tykwinski J. Org. Chem. 2007, 72, 9622-9629 doi:10.1021/jo701810g
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