UNPRECEDENTED RING EXPANSION OF [60]FULLERENE - INCORPORATION OF NITROGEN AT AN OPEN 6,6-RING JUNCTURE BY REGIOSPECIFIC REDUCTION OF OXYCARBONYLAZIRIDINO-[2'3' 1,2][60]FULLERENES - SYNTHESIS OF 1A-AZA-1(6A)-HOMO[60]FULLERENE, C60H2NH/

Upon treatment with zinc in glacial acetic acid, N-oxycarbonylaziridin o[2',3':1,2][60]fullerenes 3 undergo a reversible reductive cleavage o f the bridgehead C-C bond to provide the first examples of bridged ful leroids 4 having an open 6,6-ring juncture; deprotection of the N-tert -butoxycarbonyI-derivative 4a allows the convenient synthesis of C60H2 NH 5, the parent member of this new class of bridged fulleroids.