Fullerene-Based Macro-Heterocycle Prepared through Selective Incorporation of Three N and Two O Atoms into C60

A 14-membered heterocycle is created on the C-60 cage skeleton through a multistep procedure. Key steps involve repeated PCl5-induced hydroxylamino N-O bond cleavage leading to insertion of nitrogen atoms, and also piperidine-induced peroxo O-O bond cleavage leading to insertion of oxygen atoms. The hetero atoms form one pyrrole, two pyran, and one diazepine rings in conjunction with the C-60 skeleton carbon atoms. The fullerene-based macrocycle showed unique reactivities towards fluoride ion and copper salts.