Curculio incanus

Abstract

Four isomers are currently known for the trioxygenated fullerene derivative C₆₀(O)₃, three regioisomers with all of the oxygen addends as epoxy groups and the unstable ozonide isomer with a 1,2,3-trioxlane ring. Here we report the synthesis of an open-cage isomer for C₆₀(O)₃ with a ketolactone moiety embedded into the fullerene skeleton through a three-step procedure mediated by fullerene peroxide chemistry. Two fullerene skeleton carbon–carbon bonds are cleaved in the process. The open-cage derivative C₆₀(O)₃ can be converted back to C₆₀ through deoxygenation with PPh₃. Single crystal X-ray structure confirmed the open-cage structure