Ab Initio Molecular Orbital Study of Substitution on the Vinylic Carbon in F₂C=C (OMs) BMe₃^-under S_N1-like Mechanism.

Abstract

A substitution on vinylic carbon was investigated by using ab initio molecular orbital calculations at the MP2/6-31+G^*//RHF/6-31+G^* level of theory. The intrinsic reaction coordinate calculations of 2, 2-difluoro-1-mesyloxyvinyl- (trimethyl) borate showed a possibility that the substitution proceeds through S_N1-like mechanism with retention of configuration although the activation energy is as large as 56.2 kcal mol^-1 in vacuum and 36.3 kcal mol^-1 in THF.