Reductively activated "Polar" nucleophilic aromatic substitution. II. The reaction of p-dinitrobenzene and p-nitrobenzonitrile with charged and neutral nucleophiles

Electrochemical studies indicate that although the reactions of p-dinitrobenzene and p-nitrobenzonitrile with phenolate or phenol in DMF show radical features, they can not be attributed to the direct reaction of the nucleophile on the substrate radical anion. Reductive activation is feasible in certain cases (reaction of p-dinitrobenzene with phenol). However, substrate radical anion formation is not responsible for it. © 1994.