Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates: Formation and characterization of 2H-, 3H- and 4H-azepines

Kyosuke Satake, Ryoichi Okuda, Michiaki Hashimoto, Yasusi Fujiwara, Hideki Okamoto, Masaru Kimura, Shiro Morosawa

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Abstract

Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 3H-azepines. Under similar conditions, methyl 3,6-ditert-butyl-1H-azepine-1-carboxylate gave not only the 3H-azepine but also the isomerized 2H- and 4H-azepines. Application of the reaction to dimethyl and diisopropyl substituted 1H-azepines showed that bulky alkyl group substitution stabilizes the seven-membered azatriene system. The thermal behaviour of the di-tert-butyl substituted azepines is discussed.

Original languageEnglish
Pages (from-to)1753-1757
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
Publication statusPublished - 1994

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Azepines
Substitution reactions

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  • Chemistry(all)

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Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates : Formation and characterization of 2H-, 3H- and 4H-azepines. / Satake, Kyosuke; Okuda, Ryoichi; Hashimoto, Michiaki; Fujiwara, Yasusi; Okamoto, Hideki; Kimura, Masaru; Morosawa, Shiro.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 13, 1994, p. 1753-1757.

Research output: Contribution to journalArticle

Satake, Kyosuke ; Okuda, Ryoichi ; Hashimoto, Michiaki ; Fujiwara, Yasusi ; Okamoto, Hideki ; Kimura, Masaru ; Morosawa, Shiro. / Demethoxycarbonylation of methyl 2,5- and methyl 3,6-dialkyl-1H-azepine-1 carboxylates : Formation and characterization of 2H-, 3H- and 4H-azepines. In: Journal of the Chemical Society, Perkin Transactions 1. 1994 ; No. 13. pp. 1753-1757.
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AU - Satake, Kyosuke

AU - Okuda, Ryoichi

AU - Hashimoto, Michiaki

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AU - Okamoto, Hideki

AU - Kimura, Masaru

AU - Morosawa, Shiro

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