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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23 Citations (Scopus)

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 - Dec 1 1994

ASJC Scopus subject areas

  • Chemistry(all)

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