Preparation of fullerenol, fullerenone, and aminofullerene derivatives through selective cleavage of fullerene C–H, C–C, C–N, and C–O bonds in fullerene-mixed peroxide derivatives

Various reactions of fullerene-mixed peroxides were investigated in an effort to explore the chemistry of functional groups on the fullerene surface. Amines convert fullerene peroxides into fullerene epoxides through SN2′ type reaction. Lewis acid catalyzed hydrolysis of fullerene epoxides led to vicinal fullerendiols, which may be oxidized into fullerendiones by diacetoxyiodobenzene (DIB). Alcohols and amines react with the adjacent dione to form acetal or hemiacetal groups through different mechanisms.