ELECTROCHEMICAL BEHAVIOR OF TRIFLUOROMETHYL-SUBSTITUTED NITROBENZENE

The electrochemical behavior of o- and m-trifluoromethylnitrobenzene in N,N-dimethylformamide was investigated employing cyclic voltammetric, polarographic, and potentiostatic techniques. These compounds undergo reduction via two polarographic steps. The first is a diffusion-controlled, one-electron transfer producing a stable anion radical. The second is an ece process producing a trifluoromethyl-substituted nitrosobenzene anion radical. Mass electrolysis experiments show the long-term electrolysis product to be trifluoromethyl-substituted azoxybenzene. Addition of hydroquinone as a source of protons enhances the formation of the nitroso intermediate. © 1969, American Chemical Society. All rights reserved.