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

doi:10.1021/jo060012o

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 journal › Article › peer-review

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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.

Original language	English (US)
Pages (from-to)	4374-4382
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	71
Issue number	12
DOIs	https://doi.org/10.1021/jo060012o
State	Published - Jun 9 2006
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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

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.",

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

year = "2006",

month = jun,

day = "9",

doi = "10.1021/jo060012o",

language = "English (US)",

volume = "71",

pages = "4374--4382",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Lewis acid promoted preparation of isomerically pure fullerenols from fullerene peroxides C60(OOt-Bu)6 and C60(O) (OOt-Bu)6

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

Y1 - 2006/6/9

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.

AB - 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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DO - 10.1021/jo060012o

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

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

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