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Issue 13, 1994
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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

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-di-tert-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.

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Article type: Paper
DOI: 10.1039/P19940001753
J. Chem. Soc., Perkin Trans. 1, 1994, 1753-1757

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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

    K. Satake, R. Okuda, M. Hashimoto, Y. Fujiwara, H. Okamoto, M. Kimura and S. Morosawa, J. Chem. Soc., Perkin Trans. 1, 1994, 1753
    DOI: 10.1039/P19940001753

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