Peroxide-Mediated Selective Cleavage of [60]Fullerene Skeleton Bonds: Towards the Synthesis of Open-Cage Fulleroid C55O5

Replacement of a pentagon in [60]fullerene with five oxygen atoms yields the open-cage compound C55O5 with five carbonyl groups on the rim of the orifice. Our attempts to synthesize such a target molecule starting from C-60 have led us to prepare the fullerene-mixed peroxides such as C-60(OO-t-Bu)(6) with all the peroxo addends surrounding the same pentagon. Further investigations of the peroxide chemistry have generated various open-cage fullerene derivatives, including the carbon monoxide encapsulated endohedral compound CO@C59O6. This Personal Account mainly discusses peroxide-based processes resulting in selective cleavage of the fullerene skeleton bonds.Chemistry, MultidisciplinarySCI(E)2ARTICLEgan@pku.edu.cn1,SI189-1981