Stilbene, anthracene, and 9-anisylidenefiuorene are reduced stepwise polarographically in anhydrous acetonitrile and in dimethylformamide. Triphenylethylene, tetraphenylethylene, styrene, and 1,1-diphenylethylene give only one reduction wave.Large-scale electrolytic reductions in these solvents indicate that carbanion intermediates exist for a short period of time. 1,2,3,4-Tetraphenylbutane and meso-diphenyl succinic acid have been prepared electrolytically from stilbene in dimethylformamide.

Quinones were found to reduce stepwise to the semiquinones and hydroquinone dianions in anhydrous dimethylformamide and acetonitrile at the dropping mercury electrode. Evidence for this behavior was the shift in the second wave brought about by the presence of water and benzoic acid and the electrolytic reductive alkylation of one example, anthraquinone, by ethyl bromide to the diethyl ether of the hydroquinone. Hydroquinones are not oxidized at the dropping mercury electrode in anhydrous acetonitrile or dimethylformamide.

The electrolytic oxidation of anilines at a rotating platinum electrode in acetonitrile in the presence of pyridine involved a two electron change and formed azobenzenes. Evidence for the mechanism was the voltammetric behavior of hydrazobenzenes, p‐phenylenediamine and 4,4'‐dimethoxyazobenzene and the formation of azobenzenes in macroscale oxidations. The behavior of anilines in the absence of pyridine was more complex since the amine acted as a base and formed a salt which was not easily oxidized. Exceptions were the weakly basic o‐nitroaniline, p‐nitroaniline, 2,4‐dinitroaniline and the reversible systems, o‐phenylenediamine and p‐phenylenediamine; two electrons were involved for these examples.

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Benzophenone, acetophenone, p-methoxyaeetophenone, benzaldehyde, and anisaldehyde are reduced stepwise polarographieally in anhydrous dimethylformamide. Large-scale electrolytic reduction of benzophenone indicates that the ketyl anion is formed as a stable intermediate since, in the presence of carbon dioxide and ethyl iodide, benzilic acid and diphenylethylcarbinol are formed, respectively. Acetophenone, benzaldehyde, and anisaldehyde form principally pinacols under these conditions. The reduction of p-methoxyacetophenone is complicated by tar formation.