Does the Reaction of Cu+ with H2O2 Give OH Radicals? A Study of Aromatic Hydroxylation

Article abstract of DOI:10.1021/jo00286a024

The reaction of Cu⁺ with H2O2 was studied by using the isomer distribution obtained with fluorobenzene, anisole, and nitrobenzene as a probe for OH radicals.The reaction with benzene in presence of 5*10^-2 M Cu²⁺ gave a maximum yield of 69percent phenol.The isomer distributions obtained with fluorobenzene, anisole, and nitrobenzene are almost identical with those obtained in the radiation-induced hydroxylation under similar conditions.In experiments with benzene and nitrobenzene we have shown that Cu³⁺ produced via Cu²⁺ + OH does not hydroxylate these aromatic compounds in neutral or weakly acidic solutions (pH 5.0 - 6.0).We therefore conclude that in the reaction of Cu⁺ with H2O2 the OH radical is the major reactive species that reacts with aromatic compounds.