The Journal of Organic Chemistry

Base-induced rearrangement of epoxides to allylic alcohols. III. Alkylidenecycloalkane oxides

B Rickborn

文献索引：Thummel,R.P.; Rickborn,B. Journal of Organic Chemistry, 1971 , vol. 36, # 10 p. 1365 - 1368

全文：HTML全文

被引用次数: 35

摘要

The lithium diethylamide induced rearrangement of a series of propylidenecycloalkane oxides to allylic alcohols exhibits marked regioselectivity, with endocyclic olefin product being formed preferentially. An exception is propylidenecyclohexane oxide which gives 95% of the alternate, tertiary allylic alcohol. A series of ethylidenecycloalkane oxides, where preference for endocyclic elimination competes with proton abstraction from primary ...