Oxidative deamination of azafulleroids into C60 by peracids

Abstract

Oxidation of azafulleroids with peracids regenerated C₆₀ depending on the N-substituents. Alkyl-substituted azafulleroids preferred the oxidation of nitrogen to afford N-oxides as possible intermediates for C₆₀ in moderate yields. Phenyl- and tosyl-substituted azafulleroids rather allowed the oxidation at the carbon cage. Theoretical calculations predicted the order of reactivity of azafulleroids as well as the relative N/C nucleophilicity.