The Journal of Organic Chemistry

Fluorosulfonation. Insertion of sulfur trioxide into allylic carbon-fluorine bonds

CG Krespan, DA Dixon

Index: Krespan, Carl G.; Dixon, David A. Journal of Organic Chemistry, 1986 , vol. 51, # 23 p. 4460 - 4466

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Citation Number: 20

Abstract

Insertion of sulfur trioxide into allylic CF 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 ...