ICCAS OpenIR
Preparation of a 12-Membered Open-Cage Fullerendione through Silane/Borane-Promoted Formation of Ketal Moieties and Oxidation of a Vicinal Fullerendiol
Zhang, Gang1; Zhang, Qianyan1; Jia, Zhenshan1; Liang, Sisi2; Gan, Liangbing1,2; Li, Yuliang1
2011-08-19
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume76Issue:16Pages:6743-6748
Abstract[60]Fullerene mixed peroxide C(60) (OH)(Cl)(OOtBu) reacts with PhMe(2)SiH/B(C(6)F(5))(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/hemilcetal moieties by BF(3)-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.
DOI10.1021/jo201143k
Indexed BySCI ; IC
Language英语
WOS IDWOS:000293759000027
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/71506
Collection中国科学院化学研究所
Corresponding AuthorGan, Liangbing
Affiliation1.Chinese Acad Sci, Inst Chem, CAS Key Lab Organ Solids, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
2.Peking Univ, Coll Chem & Mol Engn, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Zhang, Gang,Zhang, Qianyan,Jia, Zhenshan,et al. Preparation of a 12-Membered Open-Cage Fullerendione through Silane/Borane-Promoted Formation of Ketal Moieties and Oxidation of a Vicinal Fullerendiol[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(16):6743-6748.
APA Zhang, Gang,Zhang, Qianyan,Jia, Zhenshan,Liang, Sisi,Gan, Liangbing,&Li, Yuliang.(2011).Preparation of a 12-Membered Open-Cage Fullerendione through Silane/Borane-Promoted Formation of Ketal Moieties and Oxidation of a Vicinal Fullerendiol.JOURNAL OF ORGANIC CHEMISTRY,76(16),6743-6748.
MLA Zhang, Gang,et al."Preparation of a 12-Membered Open-Cage Fullerendione through Silane/Borane-Promoted Formation of Ketal Moieties and Oxidation of a Vicinal Fullerendiol".JOURNAL OF ORGANIC CHEMISTRY 76.16(2011):6743-6748.
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