Thermolytic conversion of an acetamido-substituted cyclopropane into a cyclopentenone. Crystal and molecular structures of 2-Spiro-substituted Benzofuran-3-ones

Abstract

The thermolysis of an N-methylacetamido cyclopropane, spiro-substituted by a benzofuran-3-one moiety, was found to result in the elimination of methylamine and the formation of the correspondingly spiro-substituted cyclopentenone. The structures of starting material and product were determined by single-crystal X-ray diffraction methods and a mechanism for the elimination/ring enlargement reaction is proposed on the basis of the X-ray results.