Regioselective Radical Reaction of Monometallofullerene Y@C(2v)(9)-C(82) With N-arylbenzamidine Mediated by Silver Carbonate

A novel radical reaction of monometallofullerene Y@C(2v)(9)-C(82) with N-arylbezamidine (1) is successfully conducted through catalysis with silver carbonate. The high-performance liquid chromatographic and mass spectrum results demonstrate that the reaction is highly regioselective to afford only one monoadduct (2) with an imidazoline group added on C(82) cage, and computations through density functional theory reveal the addition group is attached to a specific [5, 6]-bond (C20-C76) near the Y atom. Furthermore, the analysis of prymidalization angle of the carbon atoms demonstrates the geometry of carbon cage is in favor of the regioselective formation of isomer (20, 76).