CLEMMENSEN REDUCTION .10. THE SYNTHESIS AND ACIDOLYSIS OF SOME ARYL ALKYL SUBSTITUTED CYCLOPROPANE-1,2-DIOLS

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 alpha-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.