Elimination of hydrogen fluoride from fluorinated succinic acids. (III) kinetics of dehydrofluorination of erythro- and threo-α-bromo-α′-fluorosuccinic acids

Abstract

Treatment of erythro - and threo -α-bromo-α′-fluorosuccinic acids with aqueous alkali results in the elimination of hydrogen fluoride in preference to hydrogen bromide and gives almost exclusively bromofumaric acid. The elimination of hydrogen fluoride from the two above-mentioned acids is faster by 1–2 orders of magnitude than the elimination of hydrogen fluoride from any fluorinated succinic acids. Kinetic data based on 1H NMR measurements are presented and possible mechanisms and stereochemistry involved are discussed.