Oxidative cage opening in the C70 fullerene facilitated by preceding trifluoromethylation

Abstract

Two novel derivatives of the C₇₀ fullerene with 9- and 10-membered cage openings were obtained by means of oxidation and decarbonylation of C₇₀(CF₃)₈. The major product, C₇₀(O)(CF₃)₈O₂, features a cleaved C–C bond transformed into two carbonyl functions plus an ether bridge. The second product, C₆₉O(CF₃)₈O, 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 N-oxide.