Fluorosulfonation. Insertion of Sulfur Trioxide into Allylic C-F Bonds

Article abstract of DOI:10.1021/jo00373a023

Insertion of sulfur trioxide into allylic C-F bonds of both terminal and internal fluoro olefins is shown to form the most stable olefinic products.A mechanism involving fluoroallyl cations as intermediates is proposed.State-of-the-art ab initio calculations of the ground-state energies for two isomeric unsaturated fluoro ethers establish the slightly greater stability (5.7 kcal/mol) of a vinyl ether over the corresponding fluoro olefin.A description of the optimized geometries of these molecules is also presented.