Fullerene peroxides in cage-opening reactions

Gan, Liangbing

doi:10.1351/pac200678040841

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

http://dx.doi.org/10.1351/pac200678040841

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)(OO^tBu)₄ and C₆₀(OO^tBu)₆ are effective precursors for cage-opened fullerene derivatives. Lewis acids induce the heterolysis of peroxo O-O bond in C₆₀(O)(OO^tBu)₄. Subsequent Hock-type rearrangement affords both [5,6]- and [6,6]-fullerene hemiketals - oxahomofullerene. Photolysis of C₆₀(OO^tBu)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.