Preparation of Azafullerene C59NR5 and Fullerene Derivative C60NAr5 with a Pyridine Moiety on the Cage Skeleton

[60]­Fullerene hexaadducts C60R5Cl (R = OMe or Ar) reacted with hydroxylamine to form C60R5(NHOH) with the hydroxylamino group attached on the central pentagon as in the starting material. Further reactions including treatment with PCl5 and basic alumina led to the insertion of the nitrogen atom into the fullerene cage skeleton and decarbonylation to form azafullerenes C59N­(H)­(OMe)4 and C59N­(OMe)5. The fullerene derivatives C59N­(CO)­R5 and C60NAr5 with a pyridinone and a pyridine moiety on the cage skeleton, respectively, were also synthesized starting from the hydroxylamine adducts.