Reactions of carboxylic acids with dichloro- and dibromo-alkanes in the presence of fluoride ions: effects of very strong hydrogen bonding

Abstract

Although carboxylic acids do not react with simple dihalogenated alkanes under reflux conditions, in the presence of potassium fluoride they form diesters. The role of the fluoride is to activate the nucleophilicity of the carboxylic acid by the formation of a very strong hydrogen bond with the hydroxy-group. A number of combinations of halide and acid have been studied and the important factors influencing the extent of reaction have been deduced.