Studies in bicyclo[3.1.0]hexane methanolysis. Ring opening of activated cyclopropanes under acidic and basic conditions |
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| Authors: | Lim Yeon-Hee McGee Kevin F Sieburth Scott McN |
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| Affiliation: | Department of Chemistry, 1901 N. 13th Street, Temple University, Philadelphia, Pennsylvania 19122, USA. |
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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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