Fullerene peroxides in cage-opening reactions

被引：12

作者：

Gan, LB ^{[1
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[2] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

PURE AND APPLIED CHEMISTRY | 2006年 / 78卷 / 04期

关键词：

fullerenes; peroxide; hemiketals; epoxides; ketones;

D O I：

10.1351/pac200678040841

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fullerene-mixed peroxides C-60(O)(OO'Bu)(4) and C-60((OOBu)-Bu-t)(6) are effective precursors for cage-opened fullerene derivatives. Lewis acids induce the heterolysis of peroxo O-O bond in C-60(O)((OOBu)-Bu-t)(4). Subsequent Hock-type rearrangement affords both [5,6]- and [6,6]-fullerene hemiketals-oxahomofullerene. Photolysis of C-60((OOBu)-Bu-t)(6) results in the homolysis of O-O and C-O bonds, affording fullerene diketone as the major product. Spectroscopic data and single-crystal analysis confirmed the cage-opening reactions.

引用

页码：841 / 845

页数：5

共 20 条

[1]

ANDO W, 1992, ORGANIC PEROXIDES, P174

[2] Triple scission of a six-membered ring on the surface of C-60 via consecutive pericyclic reactions and oxidative cobalt insertion [J].

Arce, MJ ;

Viado, AL ;

An, YZ ;

Khan, SI ;

Rubin, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (15) :3775-3776

[3] HOLEY FULLERENES - A BIS-LACTONE DERIVATIVE OF [70]FULLERENE WITH AN 11-ATOM ORIFICE [J].

BIRKETT, PR ;

AVENT, AG ;

DARWISH, AD ;

KROTO, HW ;

TAYLOR, R ;

WALTON, DRM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1869-1870

[4] Fullerenes as a tert-butylperoxy radical trap, metal catalyzed reaction of tert-butyl hydroperoxide with fullerenes, and formation of the first fullerene mixed peroxides C60(O)(OOtBu)4 and C70(OOtBu)10 [J].

Gan, LB ;

Huang, SH ;

Zhang, XA ;

Zhang, AX ;

Cheng, BC ;

Cheng, H ;

Li, XL ;

Shang, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13384-13385

[5] Preparation of [5,6]- and [6,6]-oxahomofullerene derivatives and their interconversion by lewis acid assisted reactions of fullerene mixed peroxides [J].

Huang, SH ;

Xiao, Z ;

Wang, FD ;

Zhou, J ;

Yuan, G ;

Zhang, SW ;

Chen, ZF ;

Thiel, W ;

Schleyer, PV ;

Zhang, X ;

Hu, XQ ;

Chen, BC ;

Gan, LB .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (18) :5449-5456

[6] Selective preparation of oxygen-rich [60]fullerene derivatives by stepwise addition of tert-butylperoxy radical and further functionalization of the fullerene mixed peroxides [J].

Huang, SH ;

Xiao, Z ;

Wang, FD ;

Gan, LB ;

Zhang, X ;

Hu, XQ ;

Zhang, SW ;

Lu, MJ ;

Pan, QQ ;

Xu, L .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2442-2453

[7]

Hummelen JC, 1999, TOP CURR CHEM, V199, P93

[8] THERE IS A HOLE IN MY BUCKY [J].

HUMMELEN, JC ;

PRATO, M ;

WUDL, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (26) :7003-7004

[9] A bowl-shaped fullerene encapsulates a water into the cage [J].

Iwamatsu, S ;

Uozaki, T ;

Kobayashi, K ;

Re, SY ;

Nagase, S ;

Murata, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2668-2669

[10]

KARFUNKEL HR, 1992, J COMPUT AID MOL DES, V6, P512

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