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 Scopus citations

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

ASJC Scopus subject areas

  • Organic Chemistry

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