Studies in Bicyclo[3.1.0]hexane Methanolysis. Ring Opening of Activated Cyclopropanes under Acidic and Basic Conditions
The Journal of Organic Chemistry2002Vol. 67(18), pp. 6535–6538
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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.
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