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Synthesis 1995; 1995(3): 253-260
DOI: 10.1055/s-1995-3902
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On the Reaction of α-Chlorocarbenium Ions with Sulfinylamines

André Voges, Atef Hamed, Amal Ahmed El-Badry, Abdel-Hamid Ismail, Johannes C. Jochims*
  • *Fakultät für Chemie der Universität Konstanz, Postfach 5560-733, D-78434 Konstanz, Germany
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Publication Date:
31 December 2000 (online)

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Aryl-, and vinyltrichloromethanes 1 are transformed with antimony pentachloride to α,α-dichlorocarbenium salts 2, which react with sulfinylamines 3 to afford nitrilium salts 4 in good yields. In contrast to this preparatively useful reaction, the reaction of α-monochlorocarbenium ions 8 (obtained from diaryldichloromethanes 7) with sulfinylamines 3 affords mixtures of iminium salts 10, isoindolium salts 13, and 2-azoniaallene salts 14.

nitrilium salts - isoindolium salts - α,α-dichlorocarbenium salts - diarylchlorocarbenium salts - sulfinylamines