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.
Keywords: fullerenes; peroxide; hemiketals; epoxides; ketones.
*Paper based on a presentation at the 11th International Symposium on Novel Aromatic Compounds (ISNA-11), St. John's, Newfoundland, Canada, 14-18 August 2005. Other presentations are published in this issue, pp. 685-888..