Manganese(Ⅲ) acetate-mediated radical reaction of [60]fullerene with bromoacetic acid,3-chloropropionic acid or 1-naphthylacetic acid

被引：0

作者：

LI FaBao1

2 State Key Laboratory of Applied Organic Chemistry

机构：

来源：

Science Bulletin | 2010年 / 25期

基金：

中国博士后科学基金; 高等学校博士学科点专项科研基金;

关键词：

60]fullerene; manganese(III) acetate; carboxylic acids; C60-fused lactones;

D O I：

暂无

中图分类号：

O621.25 [];

学科分类号：

070303 ; 081704 ;

摘要：

The manganese(Ⅲ) acetate-mediated radical reaction of [60]fullerene (C60) with three carboxylic acids,that is,bromoacetic acid,3-chloropropionic acid,and 1-naphthylacetic acid,was investigated. The reaction of C60 with bromoacetic acid in the presence of 4-(dimethylamino)pyridine afforded the anticipated C60-fused lactone,while the reaction with 3-chloropropionic acid unexpectedly led to the formation of a novel C60-fused lactone with the loss of one molecule of HCl. Interestingly,the reaction with 1-naphthylacetic acid under similar conditions gave both C60-fused lactone and 1,4-adduct,yet each of them could be selectively obtained by controlling reaction conditions. It was also observed that the C60-fused lactone bearing a bulky naphthyl group existed as two isomers.

引用

页码：2909 / 2914

页数：6

共 5 条

[1]

Cycloaddition to buckminsterfullerene C60: advancements and future prospects[J] . M. A. Yurovskaya,I. V. Trushkov.Russian Chemical Bulletin . 2002 (3)

[2] Activated carbon as the reagent for the oxidative cyclization of fullerene adducts [J].

Bernstein, R ;

Foote, CS .

TETRAHEDRON LETTERS, 1998, 39 (39) :7051-7054

[3] ADDITION-REACTIONS OF BUCKMINSTERFULLERENE (C-60) [J].

HIRSCH, A .

SYNTHESIS-STUTTGART, 1995, (08) :895-913

[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 C(60)(O)(OO(t)Bu)(4)and C(70)(OO(Bu)(10) .2 L.-B.Gan,S.-H.Huang,X.Zhang,A.-X.Zhang,B.-C.Cheng,H.Cheng,X.-L.Li,and G.Shang. J.Am.Chem.Soc . 2002

[5]

Cu(II) acetate- and Mn(III) acetate-mediated radical reactions of[60]fullerene with ketonic compounds .2 Wang G W,Li F B. Org Bio- mol Chem . 2005

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