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

Al-Talib, Mahmoud; Zaki, Magdi; Hehl, Sabine; Stumpf, Rüdiger; Fischer, Helmut; Jochims, Johannes

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

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Date

1996

Authors

Al-Talib, Mahmoud

Zaki, Magdi

Hehl, Sabine

Stumpf, Rüdiger

Fischer, Helmut

Jochims, Johannes

Publication type

Journal article

Published in

Synthesis ; 1996 (1996), 09. - pp. 1115-1121. - ISSN 0039-7881. - eISSN 1437-210X

Abstract

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.

Subject (DDC)

540 Chemistry

Keywords

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

Cite This

ISO 690

AL-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(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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