Computational study of electrophilic addition to acrylate anion:cyclic halonium is the transition structure for degenerate rearrangement of alpha-lactones.
The cyclic chloronium or bromonium carboxylate obtained by addition of Cl+ or Br+ to acrylate anion is shown by PCM/B3LYP/6-31+G* calculations to be not an intermediate but a transition structure for interconversion of equivalent halomethyl oxiranones.
Department of Chemistry, University of Bath, Bath, UK BA2 7AY.
Giuseppe D
GD
Ruggiero
Ian H
IH
Williams