Reaction of Halogenonitrobenzenes with Electro-generated Superoxide Ion

Article abstract of DOI:10.1246/bcsj.53.2188

The reaction of halogenonitrobenzenes (XNBs) with electrogenerated superoxide ion in N,N-dimethylformamide was studied electrochemically using cyclic voltammetry (CV) and controlled potential macro-electrolysis.It was shown in the CV that electro-generated superoxide ion reacts with all the o-and p-imorers of iodo-, bromo-, and chloronitrobenzene in the dissolved oxygen medium.However the superoxide ion did not react with the other XNBs during CV.Controlled potential macro-electrolysis of oxygen in the presence of o- and p-bromo-nitrobenzene yielded the corresponding nitriphenols as the main products.The reaction mechanism via nucleophilic attack of the superoxide ion on the XNB, in the preference to an electron-transfer mechanism, is proposed.