ELECTROCHEMICAL OXIDATION OF TETRAMETHYLHYDRAZINE, 1,1-DIMETHYL-2,2-DIBENZYLHYDRAZINE AND TETRABENZYLHYDRAZINE

Cyclic voltammetric studies of the title hydrazines have shown that the first step of oxidation yields stable radical cations. Though the electron transfer reaction is somewhat slow and very dependent on surface condition when solid electrodes are used, the process is quite reversible at mercury electrodes. Chemical analyses of electrolysis solutions were used to supplement rotating ring-disk voltammetric studies of the second stage of oxidation. The initially formed dication undergoes rapid deprotonation and the protons so formed can react with incoming starting material reducing the currents observed below the two-electron level. Deprotonation of the dication at an α-carbon gives a postulated cationic intermediate which can undergo two reactions whose products were observed: dealkylation to form a hydrazone and deprotonation with N-N cleavage giving an imine. © 1979 Elsevier Sequoia S.A.