Journal of the Chemical Society. Perkin transactions II p. 1211 - 1216 (1986)
Update date:2022-08-04
Topics:
Banks, Malcolm R.
Hudson, Robert F.
The reaction of several N-methylhydroxamic acids with methane- and benzene-sulphinyl chloride is shown to give an isolatable O-sulphinylated intermediate (IV) below 0 deg C.The intermediates decompose at ambient temperatures with simultaneous N-O and S-O bond fission to give the isomeric N-acyl-N-methylsulphonamide (V) and N-methyl-O-sulphonylhydroxamic acid (VI) by in-cage and free pair radical recombination. 1H and 13C n.m.r. spectra show strong polarisations in both sulphonamide (V) and O-sulphonylhydroxamic acid (VI), indicating radical cage mechanisms.In addition, a strong e.s.r. signal was observed due to the N-acyl- N-methylnitroxyl radical (X).
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