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

Dateien

Zu diesem Dokument gibt es keine Dateien.

Datum

1996

Autor:innen

Al-Talib, Mahmoud

Zaki, Magdi

Hehl, Sabine

Stumpf, Rüdiger

Fischer, Helmut

Jochims, Johannes

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Synthesis. 1996, 1996(09), pp. 1115-1121. ISSN 0039-7881. eISSN 1437-210X. Available under: doi: 10.1055/s-1996-4340

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.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

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

Zitieren

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, 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}
}

RDF

<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/23075">
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dcterms:issued>1996</dcterms:issued>
    <dcterms:abstract xml:lang="eng">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.</dcterms:abstract>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:rights>terms-of-use</dc:rights>
    <dc:contributor>Al-Talib, Mahmoud</dc:contributor>
    <dc:creator>Jochims, Johannes</dc:creator>
    <dc:contributor>Hehl, Sabine</dc:contributor>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/23075"/>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Al-Talib, Mahmoud</dc:creator>
    <dc:contributor>Stumpf, Rüdiger</dc:contributor>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2013-06-19T07:42:20Z</dcterms:available>
    <dc:language>eng</dc:language>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
    <dc:contributor>Fischer, Helmut</dc:contributor>
    <dc:creator>Zaki, Magdi</dc:creator>
    <dc:creator>Hehl, Sabine</dc:creator>
    <dc:creator>Fischer, Helmut</dc:creator>
    <dc:creator>Stumpf, Rüdiger</dc:creator>
    <dc:contributor>Zaki, Magdi</dc:contributor>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2013-06-19T07:42:20Z</dc:date>
    <dc:contributor>Jochims, Johannes</dc:contributor>
    <dcterms:bibliographicCitation>Synthesis ; (1996), 9. - S. 1115 - 1121</dcterms:bibliographicCitation>
    <dcterms:title>Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones</dcterms:title>
  </rdf:Description>
</rdf:RDF>

Universitätsbibliographie

Nein