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

doi:10.3987/COM-03-9851

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

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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 language	English
Pages (from-to)	2211-2215
Number of pages	5
Journal	Heterocycles
Volume	60
Issue number	10
DOIs	https://doi.org/10.3987/COM-03-9851
Publication status	Published - Oct 1 2003

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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

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.",

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T1 - Plausible mechanism for the formation of 2-methoxy-2H-azepine derivatives from 3H-azepines using bromine and NBS

AU - Satake, Kyosuke

AU - Cordonier, Christopher

AU - Kubota, Yasuhiro

AU - Jin, Yuexian

AU - Kimura, Masaru

PY - 2003/10/1

Y1 - 2003/10/1

N2 - 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.

AB - 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.

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

Abstract

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