Favorskii重排

可以烯醇化的α-卤代酮在烷氧基,羟基或胺催化下重排分别生成酯,羧酸或酰胺的反应。

环状底物的Favorskii重排

反应机理

烯醇化的α-卤代酮进行分子内的SN2反应得到环丙酮中间体,亲核试剂进攻环丙酮的羰基进行重排生成产物。

反应实例

参考文献

1. (a) Favorskii, A. E. J. Prakt. Chem. 1895, 51, 533􀀐563. Aleksei E. Favorskii

(1860-􀀐1945), born in Selo Pavlova, Russia, studied at St. Petersburg State University, where he became a professor since 1900. (b) Favorskii, A. E. J. Prakt. Chem. 1913,88, 658.

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12. Filipski, K.J.; Pfefferkorn, J. A. Favorskii Rearrangement. In Name Reactions forHomologations-Part II; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 238􀀐252. (Review).

13. Kammath, V. B.; Šolomek, T.; Ngoy, B. P.; Heger, D.; Klán, P.; Rubina, M.; Givens,R. S. J. Org. Chem. 2013, 78, 1718–1729.

编译自:J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Favorskii rearrangement7page 239-241.

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