Reaction between N,N-dialkylhydroxylamines and sulphinyl chlorides

Abstract

The reactions of several N,N-dialkylhydroxylamines with methane- and benzene-sulphinyl chlorides below O °C give O-sulphinylated intermediates. These rearrange at ambient temperatures to give the corresponding sulphonamides and in some cases the imines and products derived from the decomposition of the accompanying sulphinic acids. N.m.r. spectra (¹H and ¹³C) show strong polarizations in the sulphonamides, indicating a radical-cage mechanism. No CIDNP signals were observed in the imines, which can be formed in a six-electron symmetry-allowed cyclic elimination.