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

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).