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.
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