Clemmensen Reduction. X. The Synthesis and Acidolysis of Some Aryl Alkyl Substituted Cyclopropane-1,2-diols
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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.
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2011 ◽
Vol 90-93
◽
pp. 2389-2392
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