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N-acyliminium salts from the reaction of nitrilium salts with aldehydes

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1991

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Glocker, Michael O.
Hofmann, Josef

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http://nbn-resolving.de/urn:nbn:de:bsz:352-234887
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https://doi.org/10.1016/S0040-4020(01)80917-0
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Tetrahedron. 1991, 47(2), pp. 205-218. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/S0040-4020(01)80917-0

Zusammenfassung

The nitrilium hexachloroantimonates 2a,d,g,p react with aromatic aldehydes to give isolable N-acyliminium hexachloroantimonates 10a-m. The N-aroyliminium salts (10g-m) and acyliminium salts with an aliphatic N-acyl group (10a-f) are of remarkably different stability. Contrary to the N-aroyliminium salts, compounds 10a-f are unstable in solution, e. g. react immediately with acetonitrile. With excess of aldehyde 10n,o give insertion products of the probable structures 12a,b. For 10b,f X-ray structural analyses have been carried out. The N-acylcyanamidium hexachloroantimonate 2p reacts with aldehydes to give new classes of cyclic N-acyliminium salts 13a-f, and 14f, respectively.

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540 Chemie

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ISO 690JOCHIMS, Johannes, Michael O. GLOCKER, Josef HOFMANN, Helmut FISCHER, 1991. N-acyliminium salts from the reaction of nitrilium salts with aldehydes. In: Tetrahedron. 1991, 47(2), pp. 205-218. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/S0040-4020(01)80917-0
BibTex
@article{Jochims1991Nacyl-23488,
  year={1991},
  doi={10.1016/S0040-4020(01)80917-0},
  title={N-acyliminium salts from the reaction of nitrilium salts with aldehydes},
  number={2},
  volume={47},
  issn={0040-4020},
  journal={Tetrahedron},
  pages={205--218},
  author={Jochims, Johannes and Glocker, Michael O. and Hofmann, Josef and Fischer, Helmut}
}
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    <dcterms:abstract xml:lang="eng">The nitrilium hexachloroantimonates 2a,d,g,p react with aromatic aldehydes to give isolable N-acyliminium hexachloroantimonates 10a-m. The N-aroyliminium salts (10g-m) and acyliminium salts with an aliphatic N-acyl group (10a-f) are of remarkably different stability. Contrary to the N-aroyliminium salts, compounds 10a-f are unstable in solution, e. g. react immediately with acetonitrile. With excess of aldehyde 10n,o give insertion products of the probable structures 12a,b. For 10b,f X-ray structural analyses have been carried out. The N-acylcyanamidium hexachloroantimonate 2p reacts with aldehydes to give new classes of cyclic N-acyliminium salts 13a-f, and 14f, respectively.</dcterms:abstract>
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