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Pure Appl. Chem., 2006, Vol. 78, No. 4, pp. 841-845

Fullerene peroxides in cage-opening reactions

Liangbing Gan

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Peking University, Beijing 100871, China; State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China

Abstract: Fullerene-mixed peroxides C60(O)(OOtBu)4 and C60(OOtBu)6 are effective precursors for cage-opened fullerene derivatives. Lewis acids induce the heterolysis of peroxo O-O bond in C60(O)(OOtBu)4. Subsequent Hock-type rearrangement affords both [5,6]- and [6,6]-fullerene hemiketals - oxahomofullerene. Photolysis of C60(OOtBu)6 results in the homolysis of O-O and C-O bonds, affording fullerene diketone as the major product. Spectroscopic data and single-crystal analysis confirmed the cage-opening reactions.