Configuration, Conformation, and Dynamics of Octalene

Authors

  • Prof. Dr. Jean F. M. Oth,

    Corresponding author
    1. Laboratorium für Organische Chemie der Eidgenössischen Technischen, Hochschule, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
    • Laboratorium für Organische Chemie der Eidgenössischen Technischen, Hochschule, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
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  • Priv.-Doz. Dr. Klaus Müllen,

    1. Laboratorium für Organische Chemie der Eidgenössischen Technischen, Hochschule, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
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  • Dipl.-Chem. Hans-Volker Runzheimer,

    1. Institut für Organische Chemie der Universität, Greinstrasse 4, D-5000 Köln 41 (Germany)
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  • Peter Mues,

    1. Institut für Organische Chemie der Universität, Greinstrasse 4, D-5000 Köln 41 (Germany)
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  • Prof. Dr. Emanuel Vogel

    1. Institut für Organische Chemie der Universität, Greinstrasse 4, D-5000 Köln 41 (Germany)
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Abstract

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The synthesis, structure, and properties of octalene are described for the first time. This [8]annuleno[8]annulene, accessible in many steps from a tetrahydronaphthalene, is a lemon yellow hydrocarbon that is very air-sensitive. Independent structural proof was obtained by crystal structure analysis of a triazolinedione adduct. Examination of the 13C-NMR spectra at +120, +25, and −150°C ruled out the form with a central double bond and the aromatic form. The temperature dependence of the spectrum indicates mutually independent inversions of the cyclooctatetraene and the cyclooctatriene fragments. The peripheral π-bonds undergo shifts above about 80°C. The transition state is planar.

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