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
Publication statusPublished - Oct 1 2003

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Azepines
Bromine
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Satake, K., Cordonier, C., Kubota, Y., Jin, Y., & Kimura, M. (2003). Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS. Heterocycles, 60(10), 2211-2215.

Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS. / Satake, Kyosuke; Cordonier, Christopher; Kubota, Yasuhiro; Jin, Yuexian; Kimura, Masaru.

In: Heterocycles, Vol. 60, No. 10, 01.10.2003, p. 2211-2215.

Research output: Contribution to journalArticle

Satake, K, Cordonier, C, Kubota, Y, Jin, Y & Kimura, M 2003, 'Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS', Heterocycles, vol. 60, no. 10, pp. 2211-2215.
Satake, Kyosuke ; Cordonier, Christopher ; Kubota, Yasuhiro ; Jin, Yuexian ; Kimura, Masaru. / Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS. In: Heterocycles. 2003 ; Vol. 60, No. 10. pp. 2211-2215.
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