Synthesis 2012; 44(15): 2347-2352
DOI: 10.1055/s-0031-1290409
paper
© Georg Thieme Verlag Stuttgart · New York

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

Xiaolei Chen
a  School of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801   Email: jmzhang@shu.edu.cn
,
Shanshan He
a  School of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801   Email: jmzhang@shu.edu.cn
,
Subo Shen
a  School of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801   Email: jmzhang@shu.edu.cn
,
Jingwei Zhao
b  Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Email: zhusz@sioc.ac.cn
,
Jianmin Zhang*
a  School of Science, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66133801   Email: jmzhang@shu.edu.cn
b  Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Email: zhusz@sioc.ac.cn
,
Shizheng Zhu*
b  Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China, Email: zhusz@sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 10 April 2012

Accepted after revision: 08 May 2012

Publication Date:
18 June 2012 (online)


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 (ArFCH2COOH). 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.

Supporting Information

 
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