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

Autoren

  • 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
Weitere Informationen

Publikationsverlauf

Received: 10. April 2012

Accepted after revision: 08. Mai 2012

Publikationsdatum:
18. Juni 2012 (online)


Graphical Abstract

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