Preparation of fullerenol, fullerenone, and aminofullerene derivatives through selective cleavage of fullerene C-H, C-C, C-N, and C-O bonds in fullerene-mixed peroxide derivatives |
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| Authors: | Zhongping Jiang Liangbing Gan Zheming Wang |
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| Institution: | a Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China |
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| Abstract: | Various reactions of fullerene-mixed peroxides were investigated in an effort to explore the chemistry of functional groups on the fullerene surface. Amines convert fullerene peroxides into fullerene epoxides through SN2′ type reaction. Lewis acid catalyzed hydrolysis of fullerene epoxides led to vicinal fullerendiols, which may be oxidized into fullerendiones by diacetoxyiodobenzene (DIB). Alcohols and amines react with the adjacent dione to form acetal or hemiacetal groups through different mechanisms. |
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