The reaction of ketoximes and amidoximes with sulphinyl chlorides at low temperatures produces the thermally unstable O-sulphinylated oximes (I), which have been characterised by 1H and 13C n.m.r. spectroscopy. At higher temperatures, the products are the thermally stable N-sulphonylimines (II), produced by thermal rearrangement of compounds (I). The rearrangement of (I) to (II) has been shown, by means of e.s.r., 13C CIDNP, and kinetic studies, to involve homolytic N–O bond cleavage to give iminyl and sulphonyl radicals followed by radical recombination with N–S bond formation.
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Brown et al. (1978) studied this question.