Regioselective CF2 functionalization of Sc3N@D3h(5)-C78

Abstract

We report the first synthesis and computational study of Sc₃N@C₇₈(CF₂) – an analog of the previously reported Sc₃N@C₈₀(CF₂) with a less common carbon cage whose chemical properties presently remain far less studied. Sc₃N@C₇₈ appears to be considerably more reactive toward CF₂ addition than Sc₃N@C₈₀ and somewhat more reactive than C₆₀. Even though the less symmetric D_3h(5)-C₇₈ carbon cage offers far broader opportunities for isomerism than I_h-C₈₀, CF₂ addition to Sc₃N@C₇₈ proceeds regioselectively, similarly to other common fullerene reactions. A DFT survey of the thermodynamic and kinetic aspects of CF₂ addition demonstrates that the regioselectivity is controlled kinetically.