Polarographic Studies in Acetonitrile and Dimethylformamide

Abstract

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.