Oxidative Cleavage of Substituted Naphthalenes Induced by Irradiated Semiconductor Powders

Article abstract of DOI:10.1021/jo00185a027

Electron-rich members of a series of substituted naphthalenes react with oxygen to give ring-cleaved products upon long wave ultraviolet irradiation of TiO2 powders suspended in oxygen-saturated acetonitrile solutions of the arene.Reactivity within the series parallels trends in the oxidation potential, i.e., the species with the less positive oxidation potential appears to react more efficiently.A mechanism involving sensitized formation of the substituted naphthalene cation radical is suggested for the semiconductor-mediated photocatalysis.