We have demonstrated that NBS is able to promote the oxidation of fullerene monoradicals to form 1,4-difunctional fullerenes. The singly bonded fullerene dimers were used as fullerene monoradical precursors, which produced various 1,4-fullerenes with a wide range of functional groups in good to high yields with high regioselectivity in terms of cosolvents and nucleophiles.