Synthesis of a Delocalized Azepinium Ion and Investigation of Its Electrophilic Character

Kyosuke Satake, Yasuhiro Kubota, Christopher E J Cordonier, Hideki Okamoto, Masaru Kimura

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An isolated example: The first π-delocalized azepinium ions 2 were generated from 2H-azepines 1 and fully characterized by NMR spectroscopy. The stability of the ions was investigated by ab initio calculations. Reaction with nucleophiles led to further support of the characterization of the ions by the selective formation of 2-substituted 2H-azepines.

Original languageEnglish
Pages (from-to)736-738
Number of pages3
JournalAngewandte Chemie - International Edition
Volume43
Issue number6
DOIs
Publication statusPublished - Jan 30 2004

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Azepines
Ions
Nucleophiles
Nuclear magnetic resonance spectroscopy

Keywords

  • Ab initio calculations
  • Aromaticity
  • Azepinium
  • Heterocycles
  • Tropylium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of a Delocalized Azepinium Ion and Investigation of Its Electrophilic Character. / Satake, Kyosuke; Kubota, Yasuhiro; Cordonier, Christopher E J; Okamoto, Hideki; Kimura, Masaru.

In: Angewandte Chemie - International Edition, Vol. 43, No. 6, 30.01.2004, p. 736-738.

Research output: Contribution to journalArticle

Satake, Kyosuke ; Kubota, Yasuhiro ; Cordonier, Christopher E J ; Okamoto, Hideki ; Kimura, Masaru. / Synthesis of a Delocalized Azepinium Ion and Investigation of Its Electrophilic Character. In: Angewandte Chemie - International Edition. 2004 ; Vol. 43, No. 6. pp. 736-738.
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