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On the basis of investigation of cyclic voltammetry, EPR spectroscopy and competition experiments, the nucleophilic substitution reaction of p-dinitrobenzene with the sodium salt of ethyl α-cyanoacetate carbanion in dimethyl sulfoxide giving ethyl α-cyano- α-(p-nitrophenyl) acetate is shown to take place via the intermediacy of p-dinitrobenzene radical anion. The reaction rate goes faster than that between p-nitrohalobenzenes and the same sodium salt of ethyl α-cyanoacetate carbanion. There is an evidence for a single electron transfer mechanism.
On the basis of investigation of cyclic voltammetry, EPR spectroscopy and competition experiments, the nucleophilic substitution reaction of p-dinitrobenzene with the sodium salt of ethyl α-cyanoacetate carbanion in dimethyl sulfoxide giving ethyl α-cyano- α- (p-nitrophenyl) acetate is shown to take place via the intermediacy of p-dinitrobenzene radical anion. The reaction rate goes faster than that between p-nitrohalobenzenes and the same sodium salt of ethyl α-cyanoacetate carbanion. There is an evidence for a single electron transfer mechanism.