Reaction of cyclic. alpha.-hydroxy epoxides with a strong base: a new 1, 2-rearrangement, evidence for a carbenoid pathway.

E Doris, L Dechoux, C Mioskowski

文献索引：Doris, Eric; Dechoux, Luc; Mioskowski, Charles Journal of the American Chemical Society, 1995 , vol. 117, # 51 p. 12700 - 12704

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被引用次数: 35

摘要

Abstract: Several substituted five-and six-membered cyclic a,,!?-unsaturated ketones are readily available by treatment of the corresponding a-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1, 2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.