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.