A study of the ferrous ion-initiated SRN1 reactions of halogenoarenes with tert-butyl acetate and N-acylmorpholine enolates

Abstract

A detailed preparative study is reported of the ferrous ion-initiated S_RN1 reactions of a range of halogenoarenes with the sodium enolates of tert-butyl acetate, N-acetylmorpholine and a number of higher N-acylmorpholines. Smooth and rapid substitution occurs in many cases, and good to excellent yields were obtained of arylacetic esters or acids, arylacetamides and arylalkanamides. The broad scope and limitations of the process have been defined, and the possible role of the ferrous ion is discussed.