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

Research output: Contribution to journalArticle

24 Citations (Scopus)

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

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Fullerenes
Lewis Acids
Peroxides
Bromides
fullerenol
Single crystals
X rays

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Lewis acid promoted preparation of isomerically pure fullerenols from fullerene peroxides C60(OOt-Bu)6 and C60(O) (OOt-Bu)6. / Wang, Fudong; Xiao, Zuo; Yao, Zhipeng; Jia, Zhenshan; Huang, Shaohua; Gan, Liangbing; Zhou, Jiang; Yuan, Gu; Zhang, Shiwei.

In: Journal of Organic Chemistry, Vol. 71, No. 12, 09.06.2006, p. 4374-4382.

Research output: Contribution to journalArticle

Wang, Fudong ; Xiao, Zuo ; Yao, Zhipeng ; Jia, Zhenshan ; Huang, Shaohua ; Gan, Liangbing ; Zhou, Jiang ; Yuan, Gu ; Zhang, Shiwei. / Lewis acid promoted preparation of isomerically pure fullerenols from fullerene peroxides C60(OOt-Bu)6 and C60(O) (OOt-Bu)6. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 12. pp. 4374-4382.
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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.",
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AU - Wang, Fudong

AU - Xiao, Zuo

AU - Yao, Zhipeng

AU - Jia, Zhenshan

AU - Huang, Shaohua

AU - Gan, Liangbing

AU - Zhou, Jiang

AU - Yuan, Gu

AU - Zhang, Shiwei

PY - 2006/6/9

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N2 - 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.

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