Lewis acid promoted preparation of isomerically pure fullerenols from fullerene peroxides C60(OOt-Bu)6 and C60(O)(OOt-Bu)6.
Fullerene mixed peroxides C60(t-BuOO)6 and C60(O)(t-BuOO)6 react with Lewis acids to form various fullerenols through the partial fragmentation of t-BuOO groups. Two monohydroxyl fullerenols with the general formula C60(OH)(t-BuOO)5 and six monohydroxyl fullerenols with the general formula C60(O)(OH)(t-BuOO)5 were prepared, which are essentially the same except the location of the OH group. An additional reaction of the monohydroxyl fullerenols gave bis- and trishydroxyl fullerenols. Single-crystal X-ray structures have been obtained for the two monohydroxyl fullerenols. Other compounds are characterized by chemical correlation and their spectroscopic data. Cuprous bromide could protect the most reactive t-BuOO group from being attacked by stronger Lewis acids. The proposed mechanism mainly involves Lewis acid induced heterolysis of the peroxo O-O bond.
Wang
Fudong
F
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Xiao
Zuo
Z
Yao
Zhipeng
Z
Jia
Zhenshan
Z
Huang
Shaohua
S
Gan
Liangbing
L
Zhou
Jiang
J
Yuan
Gu
G
Zhang
Shiwei
S
D018360:Crystallography, X-Ray; D037741:Fullerenes / Q000737:chemistry* / Q000302:isolation & purification; D007536:Isomerism; D010545:Peroxides / Q000737:chemistry; D013057:Spectrum Analysis
D037741:Fullerenes; D010545:Peroxides; C108127:fullerenol; C069837:fullerene C60