Electrochemical Studies on the Reactions Following the Oxidation of N'-Acyl-N-phenylhydrazines

Abstract

N'-acyl-phenylhydrazines (R-Ph-NHNH-COR¹) were oxidized in H2O/ CH3CN (1:1) solution pH 11.5 by electrolysis or by the reaction with p- benzoquinone (Q) and the following reactions were investigated using electrochemical methods. The cathodic wave attributed to N'-acyl-N-phenyldiazenes (R-Ph-N = N-COR') was rapidly replaced by a more negative cathodic ivave (half-wave potential = 0.7 V vs. SCE). No other anodic wave was observed, except that of the oxidation of R-Ph-NHNH-COR’. N-Phenyldiazenes (R-Ph-N = NH) might be attacked by Q and R-Ph-N = N-COR' and the cathodic wave observed at - 0.7 V might be attributed to the reduction of the oxidized form of R-Ph-N = NH. The redox potential of R-Ph-N - NH is negative enough to inject electrons directly into the conduction band of silver halides.