Aromatic Nucleophilic Substitution II. The Reaction of Chlorobenzonitriles and Chloronitrobenzenes with HMPA

Abstract HMPA is known to be an efficient solvent for various anionic reactions. As a consequence of this, we recently1 became interested in using HMPA as a solvent for effecting aromatic nucleophilic substitution between chlorobenzonitriles and sodium 2,2,2-trifluoroethoxide. This application was based on earlier work reported by Shaw2 and Kornblum3 who investigated similar reactions with alkoxide ions.