Difluoroallenyl Bromide as a Wide??Ranging Difluoromethylene Cation Equivalent: SN2 Substitution of Difluoropropargyl Bromide through Sequential SE2′ and SN2 …

B Xu, GB Hammond

Index: Xu, Bo; Hammond, Gerald B. Angewandte Chemie - International Edition, 2005 , vol. 44, # 45 p. 7404 - 7407

Full Text: HTML

Citation Number: 28

Abstract

targets.[15] We have recently shown that fluorine substitution imparts profound changes to the chemistry of allenes.[16] On the basis of abinitio calculations,[17] we postulated that a vinylogous gem-difluoro-olefin, such as fluoroallene 2a (Figure 1), would be ideally suited to acting as a difluoromethylene-cation equivalent because of the opposite NBO charges in 2a (+ 0.765 on C1 and À0. 449 on C3). This charge distribution would favor a SN2' ...