Preparation of a 12-membered open-cage fullerendione through silane/borane-promoted formation of ketal moieties and oxidation of a vicinal fullerendiol

Gang Zhang, Qianyan Zhang, Zhenshan Jia, Sisi Liang, Liangbing Gan, Yuliang Li

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

[60]Fullerene mixed peroxide C60 (OH)(Cl)(OOtBu) reacts with PhMe2SiH/B(C6F5)3 to give oxahomofullerene. Mechanistic investigation indicates that the hydroxyl group in the central pentagon ring is essential to convert the tert-butylperoxo group into a ketal moiety. Migration of the silyl group and transformation of the siloxy group into a phenyl group are observed in the deprotection of the fullerene bound siloxy group. A 12-membered open-cage fullerendione was obtained through oxidation of a [6,6]-fullerendiol. This orifice could be closed to form ketal/hemiketal moieties by BF3-catalyzed reaction with methanol. All of the new fullerene derivatives were characterized by spectroscopic data, and structure of the open-cage fullerendione was also confirmed by single-crystal X-ray analysis.

Original languageEnglish (US)
Pages (from-to)6743-6748
Number of pages6
JournalJournal of Organic Chemistry
Volume76
Issue number16
DOIs
StatePublished - Aug 19 2011

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Boranes
Fullerenes
Silanes
Oxidation
Peroxides
X ray analysis
Orifices
Hydroxyl Radical
Methanol
Single crystals
Derivatives
fullerene C60

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of a 12-membered open-cage fullerendione through silane/borane-promoted formation of ketal moieties and oxidation of a vicinal fullerendiol. / Zhang, Gang; Zhang, Qianyan; Jia, Zhenshan; Liang, Sisi; Gan, Liangbing; Li, Yuliang.

In: Journal of Organic Chemistry, Vol. 76, No. 16, 19.08.2011, p. 6743-6748.

Research output: Contribution to journalArticle

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abstract = "[60]Fullerene mixed peroxide C60 (OH)(Cl)(OOtBu) reacts with PhMe2SiH/B(C6F5)3 to give oxahomofullerene. Mechanistic investigation indicates that the hydroxyl group in the central pentagon ring is essential to convert the tert-butylperoxo group into a ketal moiety. Migration of the silyl group and transformation of the siloxy group into a phenyl group are observed in the deprotection of the fullerene bound siloxy group. A 12-membered open-cage fullerendione was obtained through oxidation of a [6,6]-fullerendiol. This orifice could be closed to form ketal/hemiketal moieties by BF3-catalyzed reaction with methanol. All of the new fullerene derivatives were characterized by spectroscopic data, and structure of the open-cage fullerendione was also confirmed by single-crystal X-ray analysis.",
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AU - Jia, Zhenshan

AU - Liang, Sisi

AU - Gan, Liangbing

AU - Li, Yuliang

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N2 - [60]Fullerene mixed peroxide C60 (OH)(Cl)(OOtBu) reacts with PhMe2SiH/B(C6F5)3 to give oxahomofullerene. Mechanistic investigation indicates that the hydroxyl group in the central pentagon ring is essential to convert the tert-butylperoxo group into a ketal moiety. Migration of the silyl group and transformation of the siloxy group into a phenyl group are observed in the deprotection of the fullerene bound siloxy group. A 12-membered open-cage fullerendione was obtained through oxidation of a [6,6]-fullerendiol. This orifice could be closed to form ketal/hemiketal moieties by BF3-catalyzed reaction with methanol. All of the new fullerene derivatives were characterized by spectroscopic data, and structure of the open-cage fullerendione was also confirmed by single-crystal X-ray analysis.

AB - [60]Fullerene mixed peroxide C60 (OH)(Cl)(OOtBu) reacts with PhMe2SiH/B(C6F5)3 to give oxahomofullerene. Mechanistic investigation indicates that the hydroxyl group in the central pentagon ring is essential to convert the tert-butylperoxo group into a ketal moiety. Migration of the silyl group and transformation of the siloxy group into a phenyl group are observed in the deprotection of the fullerene bound siloxy group. A 12-membered open-cage fullerendione was obtained through oxidation of a [6,6]-fullerendiol. This orifice could be closed to form ketal/hemiketal moieties by BF3-catalyzed reaction with methanol. All of the new fullerene derivatives were characterized by spectroscopic data, and structure of the open-cage fullerendione was also confirmed by single-crystal X-ray analysis.

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