Photochemical transformations. Part XXII. Some reactions of 2,4-dinitrobenzenesulphenyl derivatives

Abstract

Aromatic sulphides were prepared by the photolysis of 2,4-dinitrobenzenesulphenyl acetate with aromatic compounds. The reaction is general and is shown to proceed via electrophilic attack by the 2,4-dinitrobenzene-sulphenium ion, or its precursor. Transfer of oxygen from the ortho-nitro-group to the sulphur atom for 2,4-dinitrobenzenesulphenyl derivatives is demonstrated under photolytic conditions. Evidence is accumulated for the formation of a nitrene type of intermediate in certain of these redox reactions.