The Pagodane Route to Dodecahedranes: Polyfunctionalized Homologous Dodecahedranes and Dodecahedrenes

Authors

  • Dipl.-Chem. Rolf Pinkos,

    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-7800 Freiburg (FRG)
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  • Dipl.-Chem. Johann-Peter Melder,

    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-7800 Freiburg (FRG)
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  • Prof. Dr. Hans Fritz,

    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-7800 Freiburg (FRG)
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  • Prof. Dr. Horst Prinzbach

    Corresponding author
    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-7800 Freiburg (FRG)
    • Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-7800 Freiburg (FRG)
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  • This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie and BASF AG. We thank Dr. D. Hunkler for NMR analyses, Dr. J. Wörth for MS analyses, Mrs. M. Luterbeck and M. Froom, G. Leonhardt and J. Leonhardt for supplying starting materials, G. Fehrenbatch for graphical work, and Dr. W.-D. Fessner and Dr. L. Knothe for helpful discussions.

  • In memoriam Hans Musso

Abstract

original image

The spherical structure of dodecahedranes can be varied by replacing the individual CC moieties of the skeleton by C(O)C groups. This enabled the synthesis of the highly symmetric diolefin 1, whose small π/π* distance manifests itself, inter alia, in a long wavelength UV absorption. The more severely strained diene 2 could not by prepared.

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