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.