Aromatic Cation Activation: Nucleophilic Substitution of Alcohols and Carboxylic Acids

Abstract

A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropyliumcation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.