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para- and ortho-Quinodimethane Intermediates with Cumulative Double Bonds

Authors

  • Prof. Dr. Henning Hopf,

    Corresponding author
    1. Institut für Organische Chemie der Technischen Universität, Hagenring 30, D-38106 Braunschweig (Germany), Telefax: Int. code + (531)391-5388
    • Institut für Organische Chemie der Technischen Universität, Hagenring 30, D-38106 Braunschweig (Germany), Telefax: Int. code + (531)391-5388
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  • Prof. Dr. Peter G. Jones,

    1. Institut fur Anorganische und Analytische Chemie der Technischen Universität Braunschweig (Germany)
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  • Dipl.-Chem. Peter Bubenitschek,

    1. Institut für Organische Chemie der Technischen Universität, Hagenring 30, D-38106 Braunschweig (Germany), Telefax: Int. code + (531)391-5388
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  • Christian Werner

    1. Institut für Organische Chemie der Technischen Universität, Hagenring 30, D-38106 Braunschweig (Germany), Telefax: Int. code + (531)391-5388
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  • New Planar π-Systems, Part 5. We thank the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie for supporting this work.–Part 4: H. Hopf, U. Hamman, G. Zimmerman, D. Rammler, J. Pure Appl. Pyrolysis1994, 29, 57–63.

Abstract

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The highly reactive intermediates 1 and 2 with cumulative double bonds in para and ortho positions, respectively, react to give products with isolated triple bonds. Intermolecular dimerization of 1 yields a paracyclophanetetrayne, which assumes two conformations in the crystal. Compound 2 reacts by intramolecular cyclization affording a highly strained cycloocta-3-ene-1,5-diyne derivative.

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