Carbanion Rearrangements. II

Abstract

2,2- Diphenylpropyllithium has been found to rearrange with phenyl migration to yield 1,2-diphenyl-1-methylethyllithium, The analogous magnesium and mercury compounds have been prepared. Unlike the lithium derivative, the Grignard reagent does not rearrange. Preparation of the organopotassium derivative leads directly to the rearranged carbanion. 2-Phenyl-2-(p-tolyl)-propyllithium has been found to rearrange with preferential phenyl migration. This and other results are interpreted as support for a carbanion rather than a free radical rearrangement mechanism. A molecular orbital treatment of the chemistry of 1,2-shifts is presented. © 1961, American Chemical Society. All rights reserved.