Electrophilic behavior of the π delocalized azepinium ion: Friedel-Crafts reactions with benzenes and five-membered aromatic heterocycles

Yasuhiro Kubota, Kyosuke Satake, Hideki Okamoto, Masaru Kimura

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

(Chemical Equation Presented) Although the reactivity of tropylium ion with aromatic substrates is low, the reaction of azepinium ion with aromatic substrates such as benzene, phenol, furan, and thiophene resulted in the formation of 2-aryl-2H-azepine as a major product. An exceptional result in the formation of ring-contracted product was observed in the reaction with pyrrole.

Original languageEnglish
Pages (from-to)5215-5218
Number of pages4
JournalOrganic Letters
Volume7
Issue number23
DOIs
Publication statusPublished - Nov 10 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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