Monatshefte fur Chemie p. 539 - 547 (1990)
Update date:2022-08-03
Topics:
Franek, Walter
Claus, Peter K.
N-Methyl- and N-unsubstituted alkansulfenamides 6, RSNHCH3 and RSNH2, without steric or electronic stabilization have been prepared by animation of 3-alkylthio-propionitriles or methyl 3-alkylthio-propanoates with O-mesitylenesulfonyl hydroxylamine or -N-methylhydroxylamine, deprotonation of the arising azasulfonium salts 3 and fast cycloelimination of acrylonitrile or methylacrylate from intermediarily formed N-methyl- or N-unsubstituted sulfimides 4.Sulfenamides 6 could be isolated as at least 90percent pure oily compounds and were characterized by spectral data (1H- and 13C-NMR, MS) and formation of sulfenimines 7 by condensation with benzaldehyde.
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(2014)Doi:10.1039/C39900001006
(1990)Doi:10.1002/oms.1210250902
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(1990)