The Journal of Organic Chemistry

Cyclopropanation of some simple olefinic compounds. By-product formation in excess Simmons-Smith reagent

IM Takakis, YE Rhodes

文献索引：Takakis,I.M.; Rhodes,Y.E. Journal of Organic Chemistry, 1978 , vol. 43, # 18 p. 3496 - 3500

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被引用次数: 11

摘要

The Simmons-Smith reaction of certain unreactive alkenes of the types CHz= CHCHzCOzR (R= H, 1; CH3, 2; CD3, 3) and CHz= CHC&CH20R'(R'= COCH3, 4; CH3, 5; H, 6) has been studied in excess diiodomethane and zinc-copper couple or zinc-mercury couple. In somb cases the initially formed cyclopropane adducts reacted further to furnish ethers, formals, and transesterification byproducts. Ester 2 gave 10 and 11; alcohol 6 afforded 12, 9, 14, ...