Regioselective Radical Reaction of Monometallofullerene Y@C2v(9)-C82 With N-arylbenzamidine Mediated by Silver Carbonate

Abstract

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).

Recent Progress on the Functionalization of Endohedral Metallofullerenes

“…The reaction is highly regioselective and affords only one mono-adduct with an imidazoline group. The theoretical calculation reveals the addition group is attached to a specific [5,6]-bond near the Y atom [77].…”

“…The reaction is highly regioselective and affords only one mono-adduct with an imidazoline group. The theoretical calculation reveals the addition group is attached to a specific [5,6]-bond near the Y atom [77]. Xu et al reported that using 1,2,4-trichlorobenzene or iodobenzene to extract the Er-based fullerene soot, Er@C 72 (C 6 H 3 Cl 2 ) and Er@C 76 (C 6 H 5 ) were obtained by free radical addition [76].…”

“…Li et al reported a novel radical reaction of Y@C 2v (9)-C 82 with N-arylbezamidine catalyzed by silver carbonate [77]. The reaction is highly regioselective and affords only one mono-adduct with an imidazoline group.…”