910620-23-4Relevant academic research and scientific papers
Clemmensen reduction. XII The synthesis and acidolysis of some diaryl-substituted cyclopropane-1,2-diols. The possible involvement of a cyclopropyl cation
Davis, Brian R.,Hinds, Mark G.
, p. 309 - 319 (2007/10/03)
The generation of a number of 1,2-diarylcyclopropane-1,2-diols is reported. Reaction of these in situ with acid gives, primarily, an α,β-unsaturated ketone in which the aryl substituent attached to the double bond is that which is best able to stabilize a benzylic cation. It is proposed that the reaction proceeds by O-protonation of the cyclopropane- 1,2-diol, followed by loss of water and opening of the resulting cyclopropyl cation and final deprotonation. Such initial O-protonation contrasts with the C-protonation normally observed in the acidolysis of cyclopropanols and other dialkyl- and alkylaryl-cyclopropane-1,2-diols.
