The interaction of toluene-p-sulphonyl azide and some β-keto-sulphoxides

Abstract

Under conditions where β-keto-sulphones (II; X = SO₂) and toluene-p-sulphonyl azide provide stable α-diazo-β-keto-sulphones (III; X = SO₂), β-keto-sulphoxides (IV) give unstable α-diazo-β-keto-sulphoxides (VII) which, by loss of nitrogen and subsequent rearrangement, yield disulphides (VI) and α-keto-acids (V; Y = H), and/or their ethyl ester, possibly from solvolysis of the intermediate α-keto-acid thiol ester (IX).