Oxidations of some mono- and bis-(toluene-p-sulphonyl)hydrazones with mercury(II) and lead(IV) acetates: interception of hydrazonometallo intermediates. Reactions of mercury(II) acetate with nitrogen compounds. Part 2

Abstract

Oxidation of benzil bis(toluene-p-sulphonyl)hydrazone with either mercury(II) or lead(IV) acetates in acetic acid gave 4,5-diphenyl-1,2,3-triazol-1-yltoluene-p-sulphonamide. An unstable hydrazono-mercury acetate intermediate was isolated from the mercury(II) reaction and it provided a model for previously postulated lead-hydrazono intermediates. Treatment of benzil toluene-p-sulphonylhydrazone with lead(IV) acetate in acetic acid gave O-acetylbenzoin in a reaction involving phenylbenzoyldiazomethane as an intermediate. Treatment of the monohydrazone with mercury(II) acetate gave bis[benzil toluene-p-sulphonylhydrazino]mercury. Regeneration of the ketone from benzophenone toluene-p-sulphonylhydrazone on treatment with lead(IV) acetate in acetic acid was confirmed.