142024-96-2Relevant academic research and scientific papers
Clemmensen Reduction. X. The Synthesis and Acidolysis of Some Aryl Alkyl Substituted Cyclopropane-1,2-diols
Davis, Brian R.,Hinds, Mark G.,Ting, Philip P. C.
, p. 865 - 875 (2007/10/02)
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.
