Synthesis of [60]fullerene derivatives with an octahedral addition pattern

Regioselective formations of [60]fullerene derivatives with octahedral addition patterns are described Via template activation with 9,10-dimethylanthracene T-h-symmetric as well as mixed C-2v-symmetric hexaadducts are obtained in one step starting from C-60 or C-2v- symmetric monoadducts in comparatively high yields. The thermally induced cycloreversion of azide from fullerotriazolines with five methano bridges in octahedral positions allows also the synthesis of the C-2v-symmetric pentaadduct C-65(COOEt)(10) in large quantities, which shows that azides can be used as protecting groups for 6-6 double bonds the remaining octahedral double bond in C-65(COOEt)(12) is by far the most reactive in the molecule, which also allows an extremely regioselective synthesis of hexaadducts with an octahedral addition pattern. The specific oxidation of the reactive octahedral double bond of C-65(COOEt)(10) leads to an unusual dioxetane formation. (C) 1996 Elsevier Science Ltd