Prato and Bingel–Hirsch cycloaddition to heptagon-containing LaSc2N@Cs(hept)-C80: importance of pentalene units

Abstract

Possible cycloaddition sites in the heptagon-containing fullerene LaSc₂N@C_s(hept)-C₈₀ are studied computationally. Thermodynamically controlled Prato addition is predicted to proceed regioselectively across the pentagon/pentagon (p/p) edges, whereas in the kinetically-controlled Bingel–Hirsch reaction the most reactive are carbons next to the p/p edge.