On the Reaction of Nitrilium and N-Acylamidinium Salts with Oximes and Other Hetero Nucleophiles

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1993
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Glocker, Michael O.
Shrestha-Davadi, Prativa Bade
Küchler-Krischun, Jonna
Hofmann, Josef
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Chemische Berichte. 1993, 126(8), pp. 1859-1865. ISSN 0009-2940. eISSN 1099-0682. Available under: doi: 10.1002/cber.19931260817
Zusammenfassung

Nitrilium salts 2 add oximes 1 to form stable alkylideneaminooxy-substituted iminium salts 4. Compounds 4 have been postulated by Meerwein as intermediates of the Beckmann rearrangement of oximes[1]. For (E)-4c an X-ray structural analysis is performed. Other intermediates of the Beckmann rearrangement are the N-acylamidinium salts 5, which are produced by the reaction of nitrilium salts with amides. As models for the transformation of 5 into amides, the end products of the Beckmann rearrangement, reactions of N-acylamidinium salts with nucleophiles, e.g. oximes, alcohols, water, amines, thiols, and benzophenone imine are studied.

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ISO 690GLOCKER, Michael O., Prativa Bade SHRESTHA-DAVADI, Jonna KÜCHLER-KRISCHUN, Josef HOFMANN, Helmut FISCHER, Johannes JOCHIMS, 1993. On the Reaction of Nitrilium and N-Acylamidinium Salts with Oximes and Other Hetero Nucleophiles. In: Chemische Berichte. 1993, 126(8), pp. 1859-1865. ISSN 0009-2940. eISSN 1099-0682. Available under: doi: 10.1002/cber.19931260817
BibTex
@article{Glocker1993React-23448,
  year={1993},
  doi={10.1002/cber.19931260817},
  title={On the Reaction of Nitrilium and N-Acylamidinium Salts with Oximes and Other Hetero Nucleophiles},
  number={8},
  volume={126},
  issn={0009-2940},
  journal={Chemische Berichte},
  pages={1859--1865},
  author={Glocker, Michael O. and Shrestha-Davadi, Prativa Bade and Küchler-Krischun, Jonna and Hofmann, Josef and Fischer, Helmut and Jochims, Johannes}
}
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    <dcterms:abstract xml:lang="eng">Nitrilium salts 2 add oximes 1 to form stable alkylideneaminooxy-substituted iminium salts 4. Compounds 4 have been postulated by Meerwein as intermediates of the Beckmann rearrangement of oximes[1]. For (E)-4c an X-ray structural analysis is performed. Other intermediates of the Beckmann rearrangement are the N-acylamidinium salts 5, which are produced by the reaction of nitrilium salts with amides. As models for the transformation of 5 into amides, the end products of the Beckmann rearrangement, reactions of N-acylamidinium salts with nucleophiles, e.g. oximes, alcohols, water, amines, thiols, and benzophenone imine are studied.</dcterms:abstract>
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