Alkyl- and Arylsulfenamides by Cyloelimination of Alkenes from Sulfimides, 3: Formation of Primary and Secondary Aliphatic Sulfenamides of Type RSNH2 or RSNHR1

Article abstract of DOI:10.1007/BF00810863

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.