Oxidative cage opening in the C fullerene facilitated by preceding trifluoromethylation.

Two novel derivatives of the C fullerene with 9- and 10-membered cage openings were obtained by means of oxidation and decarbonylation of C(CF). The major product, C(O)(CF)O, features a cleaved C-C bond transformed into two carbonyl functions plus an ether bridge. The second product, CO(CF)O, has one of the carbonyls replaced with another ether bridge. We provide a DFT analysis of the possible formation pathways to give the oxidized compounds under the action of pyridine -oxide.