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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

BR Davis, MG Hinds and PPC Ting

Australian Journal of Chemistry 45(5) 865 - 875
Published: 1992

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.

https://doi.org/10.1071/CH9920865

© CSIRO 1992

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