Studies in bicyclo [3.1. 0] hexane methanolysis. Ring opening of activated cyclopropanes under acidic and basic conditions

YH Lim, KF McGee, SMN Sieburth

Index: Lim, Yeon-Hee; McGee Jr., Kevin F.; Sieburth, Scott McN. Journal of Organic Chemistry, 2002 , vol. 67, # 18 p. 6535 - 6538

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Citation Number: 19

Abstract

A bicyclo [3.1. 0] hexane, with one cyclopropane carbon flanked by a ketone and an ester or an aldehyde, undergoes methanolysis with cleavage of one of the two activated cyclopropane bonds, depending on the reaction conditions. Acidic conditions yield primarily or exclusively a 4-methoxycyclohexane, while basic conditions yield a 3- methoxymethylcyclopentanone.