Lewis Acid Promoted Preparation of Isomerically Pure Fullerenols from Fullerene Peroxides C60(OOt-Bu)6 and C60(O)(OOt-Bu)6

• Published in: Journal of organic chemistry 2006-06, Vol.71 (12), p.4374-4382
• Main Authors: Wang, Fudong, Xiao, Zuo, Yao, Zhipeng, Jia, Zhenshan, Huang, Shaohua, Gan, Liangbing, Zhou, Jiang, Yuan, Gu, Zhang, Shiwei
• Format: Article
• Language: English
• Subjects: Chemistry; Cross-disciplinary physics: materials science; rheology; Crystallography, X-Ray; Exact sciences and technology; Fullerenes - chemistry; Fullerenes - isolation & purification; Fullerenes and related materials; diamonds, graphite; Isomerism; Kinetics and mechanisms; Materials science; Organic chemistry; Peroxides - chemistry; Physics; Reactivity and mechanisms; Specific materials; Spectrum Analysis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo060012o

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.