Reactivity and regioselectivity in Diels–Alder reactions of anion encapsulated fullerenes

Abstract

Theoretical calculations indicate that encapsulated Cl⁻, Br⁻, I⁻, or S²⁻ are located near the center of the C₆₀; however, the encapsulated F⁻ anion is slightly displaced from the center of the cage. Encapsulated N³⁻ binds with the inner surface of the carbon cage. The opposite regioselectivity of the DA reaction with [N@C₆₀]³⁻ is controlled by the distortion energy of the CPD moiety.