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The reaction between oximes and sulphinyl chlorides: a ready, low-temperature radical rearrangement process

1978; Royal Society of Chemistry; Issue: 8 Linguagem: Inglês

10.1039/p29780000822

2050-8239

Charles A. Brown, R. F. Hudson, Keith A. F. Record,

Catalytic C–H Functionalization Methods

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.