A new ring contraction rearrangement of 2,5-and 3,6-di-tert-butyl-3H-azepines to pyridine derivatives

Kyosuke Satake; Koichi Takaoka; Michiaki Hashimoto; Hideki Okamoto; Masaru Kimura; Shiro Morosawa

doi:10.1246/cl.1996.1129

A new ring contraction rearrangement of 2,5-and 3,6-di-tert-butyl-3H-azepines to pyridine derivatives

Kyosuke Satake, Koichi Takaoka, Michiaki Hashimoto, Hideki Okamoto, Masaru Kimura, Shiro Morosawa

School of Science

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

A new ring contraction reaction giving pyridine derivatives from 3,6-and 2,5-di-tert-butyl-3H-azepines was observed by a successive treatment with bromine and aqueous K₂CD₃. A plausible mechanism via azatropilium cation for the rearrangement was discussed based on the product's distribution from respective 3H-azepines.

Original language	English
Pages (from-to)	1129-1130
Number of pages	2
Journal	Chemistry Letters
Issue number	12
DOIs	https://doi.org/10.1246/cl.1996.1129
Publication status	Published - Jan 1 1996

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.1996.1129

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title = "A new ring contraction rearrangement of 2,5-and 3,6-di-tert-butyl-3H-azepines to pyridine derivatives",

abstract = "A new ring contraction reaction giving pyridine derivatives from 3,6-and 2,5-di-tert-butyl-3H-azepines was observed by a successive treatment with bromine and aqueous K2CD3. A plausible mechanism via azatropilium cation for the rearrangement was discussed based on the product's distribution from respective 3H-azepines.",

author = "Kyosuke Satake and Koichi Takaoka and Michiaki Hashimoto and Hideki Okamoto and Masaru Kimura and Shiro Morosawa",

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AU - Satake, Kyosuke

AU - Takaoka, Koichi

AU - Hashimoto, Michiaki

AU - Okamoto, Hideki

AU - Kimura, Masaru

AU - Morosawa, Shiro

PY - 1996/1/1

Y1 - 1996/1/1

N2 - A new ring contraction reaction giving pyridine derivatives from 3,6-and 2,5-di-tert-butyl-3H-azepines was observed by a successive treatment with bromine and aqueous K2CD3. A plausible mechanism via azatropilium cation for the rearrangement was discussed based on the product's distribution from respective 3H-azepines.

AB - A new ring contraction reaction giving pyridine derivatives from 3,6-and 2,5-di-tert-butyl-3H-azepines was observed by a successive treatment with bromine and aqueous K2CD3. A plausible mechanism via azatropilium cation for the rearrangement was discussed based on the product's distribution from respective 3H-azepines.

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JF - Chemistry Letters

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ER -

A new ring contraction rearrangement of 2,5-and 3,6-di-tert-butyl-3H-azepines to pyridine derivatives

Abstract

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