The Journal of Organic Chemistry

Dipole-stabilized carbanions from esters:. alpha.-oxo lithiations of 2, 6-substituted benzoates of primary alcohols

P Beak, LG Carter

Index: Beak, Peter; Carter, Linda G. Journal of Organic Chemistry, 1981 , vol. 46, # 11 p. 2363 - 2373

Full Text: HTML

Citation Number: 26

Abstract

The hypothesis that a carbonyl group bonded to a heteroatom can provide dipole stabilization for formation of a carbanion adjacent to the heteroatom has been supported for esters, thioesters, and amides by experiment and the~ ry. l-~ s~+ Both approaches also suggest that complexation of the lithium ion to the carbonyl oxygen is an important factor in the stabilization of these organolithiums. The early cases of self-addition of a-heteroatom ...