Aromatic radical anions as possible intermediates in the nucleophilic aromatic substitution (SNAr): an EPR study

Abstract

The reactions among halonitrobenzenes or polynitrobenzenes and alkoxides, thiolates or tertiary amines have provided the evidence that in a S_NAr reaction type a single electron transfer from the nucleophile to the aromatic substrate, to generate two radical species within the solvent cage, can take place to some extent. The detection of radical intermediates by EPR spectroscopy, in several S_NAr reactions, is reported.