Studies in bicyclo[3.1.0]hexane methanolysis. Ring opening of activated cyclopropanes under acidic and basic conditions

Yeon-Hee Lim; Kevin F McGee Jr; Scott McN Sieburth

doi:10.1021/jo025909+

Studies in bicyclo[3.1.0]hexane methanolysis. Ring opening of activated cyclopropanes under acidic and basic conditions

J Org Chem. 2002 Sep 6;67(18):6535-8. doi: 10.1021/jo025909+.

Authors

Yeon-Hee Lim¹, Kevin F McGee Jr, Scott McN Sieburth

Affiliation

¹ Department of Chemistry, 1901 N. 13th Street, Temple University, Philadelphia, Pennsylvania 19122, USA.

PMID: 12201777
DOI: 10.1021/jo025909+

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.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Bridged Bicyclo Compounds / chemistry*
Cyclization
Cyclopropanes / chemistry*
Hexanes / chemistry*
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Mass Spectrometry
Methanol / chemistry*
Molecular Structure

Substances

Bridged Bicyclo Compounds
Cyclopropanes
Hexanes
Methanol