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.
Oxime of III. Ten milliliters of 95% alcohol containing 0.246 g. of III, 0.167 g. of hydroxylamine hydrochloride, and 0.5 ml. of pyridine were heated to boiling. The solution was cooled, and the solid which separated was purified from 95% alcohol (m.p. 148-149°).
Aromatic nitro compounds and triarylcarbinols gave normal polarographic waves in methanesulfonic acid. Aromatic ketones and aldehydes gave waves which were complicated by maxima. Nitro compounds were reduced to the phenythydroxytamines which were rearranged by the acid to the p-aminophenols. The triarylearbinols were reduced to the triphenylmethanes under anhydrous conditions and to the free radicals in the presence of water. Ketones and aldehydes were reduced to the pinacols which, under the influence of the strong acid, underwent the pinacol rearrangement.
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