Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones
Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones
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1996
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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.
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540 Chemistry
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nitrilium salts,N-acyliminium salts,X-ray structural analysis,variable temperature NMR spectroscopy,AM1 calculations
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AL-TALIB, Mahmoud, Magdi ZAKI, Sabine HEHL, RĂ¼diger 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-1996-4340BibTex
@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, RĂ¼diger and Fischer, Helmut and Jochims, Johannes} }
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