Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones

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1996
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Al-Talib, Mahmoud
Zaki, Magdi
Hehl, Sabine
Stumpf, Rüdiger
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Zusammenfassung

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.

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540 Chemie
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nitrilium salts, N-acyliminium salts, X-ray structural analysis, variable temperature NMR spectroscopy, AM1 calculations
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ISO 690AL-TALIB, Mahmoud, Magdi ZAKI, Sabine HEHL, Rüdiger STUMPF, Helmut FISCHER, Johannes JOCHIMS, 1996. Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones. In: Synthesis. 1996, 1996(09), pp. 1115-1121. ISSN 0039-7881. eISSN 1437-210X. Available under: doi: 10.1055/s-1996-4340
BibTex
@article{AlTalib1996Synth-23075,
  year={1996},
  doi={10.1055/s-1996-4340},
  title={Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones},
  number={09},
  volume={1996},
  issn={0039-7881},
  journal={Synthesis},
  pages={1115--1121},
  author={Al-Talib, Mahmoud and Zaki, Magdi and Hehl, Sabine and Stumpf, Rüdiger and Fischer, Helmut and Jochims, Johannes}
}
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