Clemmensen Reduction. X. The Synthesis and Acidolysis of Some Aryl Alkyl Substituted Cyclopropane-1,2-diols

Abstract

The synthesis of a number of 1-alkyl-2-arylcyclopropane-1,2-diols is reported. Reductive treatment of suitably substituted 1,3-diketones gave a cyclopropanediyl diacetate from which the diol was obtained. Reaction of these diols with acid gave α- hydroxy ketones , in which an alkyl group, rather than an aryl group, was adjacent to the carbonyl function. Clemmensen reduction of the 1,3-diketones gave products of rearrangement, generally similar to those obtained by acidolysis of the cyclopropane-1,2-diols. The relationship of these results to thermochemical studies on the stability of carboxonium ions is discussed.