Synthesis and chemical reactivity of tetrahydro[60]fullerene epoxides with both amino and aryl addends

Tetrahydro[60]fullerene epoxides C60(O)Arn(NR2)4-n, n = 1, 2, have been prepared by treating 1,4-adducts C60(OH)Ph and C60(Tol)2 with cyclic secondary amines. The epoxy moieties in these mixed tetrahydro[60]fullerene epoxides were hydrolyzed into the corresponding diol derivatives, which were further oxidized into diketone open-cage fullerenes with a 10-membered orifice. A few other reactions also showed that the present tetrahydro[60]fullerene epoxides with both amino and aryl addends exhibit improved chemical reactivity over the tetraamino[60]fullerene epoxide without any aryl group. ? 2015 American Chemical Society.SCI(E)EI0ARTICLEgan@pku.edu.cn83957-39648