A Simple Route to the Intramolecular Quinhydrone of [2.2]Paracyclophanediene

Authors

  • Dipl.-Chem. Michael Stöbbe,

    1. Institut für Organische Chemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13 (FRG)
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  • Dipl.-Chem. Stephan Kirchmeyer,

    1. Institut für Organische Chemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13 (FRG)
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  • Dr. Gunadi Adiwidjaja,

    1. Institut für Organische Chemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13 (FRG)
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  • Prof. Armin de Meijere

    Corresponding author
    1. Institut für Organische Chemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13 (FRG)
    • Institut für Organische Chemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13 (FRG)
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  • This work was supported by the Stiftung Volkswagenwerk, the Fonds der Chemischen Industrie, E. Merck AG, and Chemische Werke Hüls AG. M. S. thanks the Studienstiftung des deutschen Volkes for a Promotionsstipendium.

  • Dedicated to Professor Rolf Huisgen on the occasion of his 65th birthday

Abstract

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Molecules exhibiting intramolecular charge transfer serve, among other things, as rigid models for the experimental determination of the dependence of this interaction (which is important in photosynthesis) on distance. The title compound 1 is particularly suitable for such studies. Compound 1 was obtained via a very short route by twofold addition of singlet oxygen to [2.2]paracyclophanediene.

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