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-溴代烯烃在强碱（如醇盐）作用下重排为1,2-二芳基炔。[1][2][3] [4]
反应机理
[编辑]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
[编辑]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）
参见
[编辑]参考资料
[编辑]- ^ Paul Fritsch. Ueber die Darstellung von Diphenylacetaldehyd und eine neue Synthese von Tolanderivaten. Justus Liebig's Annalen der Chemie. 1894, 279 (3): 319–323. doi:10.1002/jlac.18942790310.
- ^ Buttenberg, W. P. Condensation des Dichloracetals mit Phenol und Toluol. Justus Liebig's Annalen der Chemie. 1894, 279 (3): 324–337. doi:10.1002/jlac.18942790311.
- ^ Wiechell, H. Condensation des Dichloracetals mit Anisol und Phenetol. Justus Liebig's Annalen der Chemie. 1894, 279 (3): 337–344. doi:10.1002/jlac.18942790312.
- ^ Köbrich, G. Eliminations from Olefins. Angewandte Chemie International Edition. 1965, 4: 49–68. doi:10.1002/anie.196500491.
- ^ Rezaei, H.; Yamanoi, S.; Chemla, F.; Normant, J. F. Fritsch-Buttenberg-Wiechell Rearrangement in the Aliphatic Series. Org. Lett. 2000, 2 (4): 419–421. doi:10.1021/ol991117z.
- ^ 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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