Self-protonation upon the electroreduction of 2- and 4-nitrophenylhydroxylamines in aprotic media

Cyclic voltammetry and controlled potential electrolysis were used to show that radical anions of 2- and 4-nitrophenylhydroxylamines electrochemically generated in a 0.1M Bu₄NClO₄ solution in DMF undergo protonation with the starting compounds (self-protonation) followed by the formation of the corresponding nitroanilines.