Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization

Christopher E.J. Cordonier, Kyosuke Satake, Hideki Okamoto, Masaru Kimura

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

2-Aryl-2H-, 3-aryl-3H-, and 4-aryl-4H-azepine were formed by the novel, electrophilic, πLUMO-controlled reaction of the 2-methoxyazepinium ion, generated in situ by the reaction of TiCl4 with 2,7-dialkoxy-2H-azepine and an aryl compound, for which the kinetic parameters of the sigmatropic hydrogen rearrangement of the 4H-azepine was measured. The substitution and hydrogen shift of the azepinium ion were analyzed with DFT studies.

Original languageEnglish
Pages (from-to)3803-3807
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Aug 25 2006

Keywords

  • 1,5-Hydrogen shift
  • 4H-Azepine
  • Azepinium
  • Density functional calculations
  • Heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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