Sulphur–nitrogen compounds: the preparation, oxidation, and decomposition of NN-bis(arylsulphonyl)hydroxylamines

Abstract

NN-Bis(arylsulphonyl)hydroxylamines, (p-XC₆H₄SO₂)₂NOH, have been prepared (X = H, Me, MeO, Cl, and F) by reaction of the corresponding benzenesulphinic acids with nitrous acid. Oxidation of the bis species with PbO₂, silver(I,III) oxide, AgO, MnO₂, Pb(O₂CMe)₄, or nitric acid yields NNO-tris(arylsulphonyl)hydroxylamines. (p-XC₆H₄SO₂)₂NOSO₂C₆H₄X-p, but HNO₂ and m-chloroperbenzoic acid do not react. infrared and n.m.r. spectra show that the tris species are hydroxylamines. R₂NOR, rather than amine oxides, R₃NO. Early work on similar compounds has been reinvestigated.