Conformational Analysis of Some 1,4-Dioxepines by Molecular Mechanics (MM2)

A. Entrena, M. A. Gallo, A. Espinosa, C. Jaime, J. Campos, J. F. Dominguez

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Abstract

The conformational analyses of 2,3-dihydro-5H-l,4-dioxepine (5), 5-methoxy-2,3-dihydro-5H-l,4-dioxepine (6), and 6,7-dihydro-5H-l,4-dioxepine (7) have been theoretically studied by molecular mechanics, indicating a preference for a twist-boat conformation in 5 and for a chair in 6 and 7. The stability of the different conformations is governed by the conjugation of the oxygen atoms with the ir system, in 5 and 7, and by this conjugation and the anomeric effect in 6. The barrier for the chair twist boat interconversion is 2.50 kcal/mol in 5 and 3.78 kcal/mol in 6. The concordance between calculated and experimental coupling constants of 5 and 6 upholds these results. © 1989, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)6034-6039
JournalJournal of Organic Chemistry
Volume54
Issue number26
DOIs
Publication statusPublished - 1 Dec 1989

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    Entrena, A., Gallo, M. A., Espinosa, A., Jaime, C., Campos, J., & Dominguez, J. F. (1989). Conformational Analysis of Some 1,4-Dioxepines by Molecular Mechanics (MM2). Journal of Organic Chemistry, 54(26), 6034-6039. https://doi.org/10.1021/jo00287a013