Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS

Kyosuke Satake, Christopher Cordonier, Yasuhiro Kubota, Yuexian Jin, Masaru Kimura

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Formation of 2-bromo-4-t-butyl-7-methoxy-2H-azepine and 4-t-butyl-7-methoxy-2-succinimidyl-2H-azepine by the respective reactions of 5-t-butyl-2-methoxy-3H-azepine with bromine and NBS suggests a plausible mechanism for the conversion of 3H-azepine to 2H-azepine as 1,4-addition of an electrophile and a consequent 1,2-dehydrobromination. Different from the case of cycloheptatriene, reaction of 3H-azepine with bromine did not give any delocalized ionic species.

Original languageEnglish
Pages (from-to)2211-2215
Number of pages5
JournalHeterocycles
Volume60
Issue number10
DOIs
Publication statusPublished - Oct 1 2003

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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