Chemical transformations on the [60] fullerene framework via aziridination processes

Isolation of closed 6,6-bridged aziridinofullerenes 2 by reaction of [60] fullerene with singlet oxycarbonylnitrenes is accompanied by small amounts of previously undetected closed 5,6-adducts 4, thought to arise by trapping of triplet nitrenes. Isomerization of the 6,6-bridged adducts to the corresponding oxazolo [4',5':1,2][60] fullerene derivatives 3 occurs upon heating with the exception of the tert-butoxycarbonyl adduct which eliminates isobutene and CO2 to yield the parent aziridinofullerene C60NH 6.