Advertisement

The Pagodane Route to Dodecahedranes: An Improved Approach to the C20H20 Parent Framework; Partial and Total Functionalizations—Does C20-Fullerene Exist?

Authors

  • Dipl.-Chem. Fabian Wahl,

    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-79104 Freiburg (FRG), Telefax: Int. code + (761)203-5987
    Search for more papers by this author
  • Dr. Jürgen Wörth,

    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-79104 Freiburg (FRG), Telefax: Int. code + (761)203-5987
    Search for more papers by this author
  • Prof. Dr. Horst Prinzbach

    Corresponding author
    1. Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-79104 Freiburg (FRG), Telefax: Int. code + (761)203-5987
    • Chemisches Laboratorium der Universität, Institut für Organische Chemie and Biochemie, Albertstrasse 21, D-79104 Freiburg (FRG), Telefax: Int. code + (761)203-5987
    Search for more papers by this author

  • This research was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemisches Industrie, and BASF AG. We thank Dr. H.-D. Beckhaus (Freiburg) for help with the calculations, Doz. Dr. E. Campbell (Max-Born-Institut für Nichtlineare Optik and Kurzzeitspektroskopie (MBI), Berlin-Adlershof (FRG)) for the laser desorption time of flight (TOF) mass spectra, and Dr. W. Vetter (Ciba-Geigy, Basel) for the FAB/FD MS analyses (FAB = fast atom bombardment, FD = field desorption, MS = mass spectrometry).

Abstract

original image

Are selective multisubstitutions on the surface of dodecahedrane possible? Can all twenty hydrogen atoms be replaced? When relatively bulky Br substituents are introduced under “mild” conditions vicinal substitution is avoided, but chlorination and bromination under “extreme” conditions gives C20Cl16 and C20Br20 (1) as the respective final products. A fragment ion generated in the mass spectrometer with m/z 240 is presumed to belong to C20-fullerene (2).

Ancillary