Health & Environmental Research Online (HERO)


Print Feedback Export to File
8209603 
Journal Article 
Configurationally and conformationally homogeneous cyclic N-aryl sulfimides. I. Synthesis and mechanism of formation 
Claus, PK; Rieder, W; Vierhapper, FW 
1978 
1 
Monatshefte für Chemie / Chemical Monthly
ISSN: 0026-9247
EISSN: 1434-4475 
Springer-Verlag 
109 
3 
609-629 
English 
Reactions of thianes and cis-and trans-1-thiadecalins with 4-chloroaniline and N-chlorsuccinimide or tert-butylhypochlorite gave configurationally homogeneous cyclic N-4-chlorophenyl sulfimides. With appropriately substituted sulfides conformationally homogeneous thiane-and cis-1-thiadecalin-1-imides were obtained. Formation of sulfimides with axially oriented S-N bond is strongly disfavoured. Reactions with conformationally rigid ring systems yielded only sulfimides with equatorial S-N bond; two isomeric sulfimides, both with equatorial S-N bond, were obtained with the mobile cis-1-thiadecalin. Sulfimides with axial S-N bond were prepared from conformationally rigid sulfoxides with equatorial S-O bond. It is assumed that formation of sulfimides with rigid ring systems proceeds via N-chloroanilines, while reactions of conformationally mobile systems with N-chlorosuccinimide may also occur via intermediate succinimidyl sulfonium ions. © 1978 Springer-Verlag.