Reactivity of an α-acyl-α-cyclopropyl-carbenium ion: a highly stereoselective cyclopropylmethyl–cyclopropylmethyl rearrangement

C Pardo, M Charpentier-Morize

Index: Pardo, Claude; Charpentier-Morize, Micheline Journal of the Chemical Society, Chemical Communications, 1982 , # 18 p. 1037 - 1039

Full Text: HTML

Citation Number: 0

Abstract

The complete stereoselectivity in a cyclopropylmethyl-cyclopropylmethyl rearrangement which has been investigated is rationalized in terms of a highly preferred conformation of the transient a-acyl-or-cyclopropyl-carbenium ion. ... The cc-acyl-or-cyclopropyl-carbenium ion (A) is destabilized ... In order to investigate the role of these two opposing factors, the silver-assisted solvolysis of compound (1) a potential pre- cursor of a carbocation of type (A), has been studied. ...