Alkyl- und Arylsulfensäureamide durch Cycloeliminierung von Alkenen aus Sulfimiden, 3: Bildung primärer und sekundärer aliphatischer Sulfenamide des TypsRSNH2 bzw.RSNHR1

Autor: Franek, Walter, Claus, Peter K.
Zdroj: Monatshefte für Chemie / Chemical Monthly; June 1990, Vol. 121 Issue: 6-7 p539-547, 9p
Abstrakt: N-Methyl- and N-unsubstituted alkansulfenamides6,RSNHCH3 andRSNH2, without steric or electronic stabilization have been prepared by amination of 3-alkylthio-proprionitriles or methyl 3-alkylthio-propanoates with O-mesitylenesulfonyl hydroxylamine or-N-methylhydroxyl-amine, deprotonation of the arising azasulfonium salts3 and fast cycloelimination of acrylonitrile or methylacrylate from intermediarily formed N-methyl- or N-unsubstituted sulfimides4. Sulfenamides6 could be isolated as at least 90% pure oily compounds and were characterized by spectral data (1H- and13C-NMR, MS) and formation of sulfenimines [bd7] by condensation with benzaldehyde.
Databáze: Supplemental Index