Synthesis of isoxazolo[60]fullerenes with dumb-bell-type structure and atropisomeric properties

New dumb-bell-type fullerene adducts 2, 4, and 8a-b could be synthesized vi a bifunctional nitrile oxides. The [60]fullerene derivative 16 of this type was synthesized by twofold esterification with an isoxazolo[60]fullerene-c arboxylic acid derivative. In the latter case the reaction was used to Link the archimedic polyhedron fullerene with the platonic element cubane. When a bulky spacer between the fullerene units was used, atropisomeres 8a-b oc curred. The fullerene derivative 11 with an anthracene moiety exhibited axi al chirality.