Sulphur–nitrogen compounds. Part 2. Reactions of (arylsulphonyl)hydroxylamines with nitrosyl chloride, nitrogen monoxide, and chlorine, and some related reactions

Abstract

The compounds RSO₂NHOH, (RSO₂)₂NOH, and RSO₂NH₂(R = Ph or p-MeC₆H₄) are all converted by nitrosyl chloride into RSO₂Cl, but (RSO₂)₂NOSO₂R and (RSO₂)₂NH are unaffected; RSO₂NHOH, (RSO₂)₂NOH, and (RSO₂)₂NOSO₂R all initiate free-radical halogenation by dichlorine and dibromine, but not by di-iodine, of benzene and cyclohexane. Oxidatron of PhSO₂NHOH by a range of oxidants yields PhSO₂Cl, PhSO₃H, or (PhSO₂)₂NOSO₂Ph, but not PhSO₂NO. The compound p-MeC₆H₄SO₂Na is converted by NOCl into p-MeC₆H₄SO₂Cl rather than to p-MeC₆H₄SO₂NO; (p-MeC₆H₄SO₂)₂NH is inert to a wide range of oxidants.