Lewis acid promoted preparation of isomerically pure fullerenols from fullerene peroxides C60(OOt-Bu)6 and C60(O) (OOt-Bu)6

Fudong Wang, Zuo Xiao, Zhipeng Yao, Zhenshan Jia, Shaohua Huang, Liangbing Gan, Jiang Zhou, Gu Yuan, Shiwei Zhang

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24 Scopus citations

Abstract

Fullerene mixed peroxides C60(t-BuOO)6 and C 60(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.

Original languageEnglish (US)
Pages (from-to)4374-4382
Number of pages9
JournalJournal of Organic Chemistry
Volume71
Issue number12
DOIs
StatePublished - Jun 9 2006

ASJC Scopus subject areas

  • Organic Chemistry

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