BIS-FUNCTIONALIZATION OF C-60 VIA THERMAL REARRANGEMENT OF AN ISOLABLE FULLEROAZIRIDINE BEARING A SOLUBILIZING SUPERMESITYL ESTER MOIETY

Heating of C-60 with the novel azidoformate 3 bearing a highly solubil ising supermesityl group affords the first example of a nitrogen-bridg ed fullerene 4 with a sigma-homoaromatic closed 6,6-aziridine structur e, which by further heating can be induced to undergo rearrangement on the fullerene surface to form as the sole product, the closed isomeri c oxazole derivative 5 with O and N vicinally bound to the fullerene f ramework at a 6,6-ring juncture