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Synthesis 1996; 1996(9): 1115-1121
DOI: 10.1055/s-1996-4340
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Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones

Mahmoud Al-Talib, Magdi Zaki, Sabine Hehl, Rüdiger Stumpf, Helmut Fischer, 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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A new method for the preparation of N-acyliminium salts 3a-ab by reaction of nitrilium salts 1 with non-enolizable alkyl and aryl ketones 2 is described. Ketones without electron-releasing substituents react only with N-arylnitrilium salts 1. An X-ray structural analysis was carried out for the N-acyliminium salt 3j. From variable temperature NMR spectroscopy intramolecular conformational changes (essentially rotation around the iminium C=N double bond, coupled to rotation about the amide C-N single bond) of few compounds 3 were determined. The observed barriers to hindered rotation are compared with barriers calculated by the AM1 method.

nitrilium salts - N-acyliminium salts - X-ray structural analysis - variable temperature NMR spectroscopy - AM1 calculations