Synthesis of Fullerene-Fused Fluorine-Containing Lactones from the Radical Reaction of [60]Fullerene with Fluorinated Phenylacetic Acids

Xiaolei Chen; Shanshan He; Subo Shen; Jingwei Zhao; Jianmin Zhang; Shizheng Zhu

doi:10.1055/s-0031-1290409

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2347-2352
DOI: 10.1055/s-0031-1290409

paper

Synthesis of Fullerene-Fused Fluorine-Containing Lactones from the Radical Reaction of [60]Fullerene with Fluorinated Phenylacetic Acids

Xiaolei Chen

^aSchool of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801 eMail: jmzhang@shu.edu.cn

,

Shanshan He

^aSchool of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801 eMail: jmzhang@shu.edu.cn

,

Subo Shen

^aSchool of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801 eMail: jmzhang@shu.edu.cn

,

Jingwei Zhao

^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, eMail: zhusz@sioc.ac.cn

,

Jianmin Zhang*

^aSchool of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801 eMail: jmzhang@shu.edu.cn

^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, eMail: zhusz@sioc.ac.cn

,

Shizheng Zhu*

^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, eMail: zhusz@sioc.ac.cn

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Abstract

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Abstract

A series of fullerene-fused fluorinated lactones were prepared by the manganese(III) acetate mediated radical reaction of [60]fullerene (C₆₀) with fluorinated phenylacetic acids (Ar_FCH₂COOH). Interestingly, the products which contain a 2-fluoro substituent on the benzene ring are mixtures of two stereoisomers due to the stereo and electronic effects of the ortho-fluorine atom.

Key words

C₆₀-fused lactones - fluorinated phenylacetic acids - manganese(III) acetate - stereoisomers

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Referenzen

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