New activating groups for poly(aryl ether) and poly(aryl sulfide) synthesis

Abstract

We have recently reported several new activating groups for nucleophilic aromatic substitution reactions and poly(aryl ether) synthesis, i.e. quinoxaline, benzoxazole and perfluoroalkyl groups. In addition, we have also begun to study the use of thiophenols as nucleophiles towards halo-, and nitroquinoxalines. Although we have not carried out detailed mechanistic studies on these transformations, it is clear there are some mechanistically unique features relative to previously reported activating groups. In this paper we will review the results of the model reactions we studied, including the effect of substituents and reaction conditions and the implications these findings have on the polymerization.