PDF herunterladen
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
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 10. April 2012

Accepted after revision: 08. Mai 2012

Publikationsdatum:
18. Juni 2012 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


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.

Key words

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

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

    • 1a Taylor R, Walton DR. M. Nature (London) 1993; 363: 685
      Crossref
    • 1b Hirsch A. Synthesis 1995; 895
      Artikel in Thieme Connect
    • 1c Diederich F, Thilgen C. Science (Washington, D.C.) 1996; 271: 317
      Crossref
    • 1d Thilgen C, Diederich F. Chem. Rev. 2006; 106: 5049
      Crossref
  • 2 Tzirakis MD, Orfanopoulos M. Org. Lett. 2008; 10: 873
    Crossref
  • 3 Zheng M, Li F.-F, Ni L, Yang W.-W, Gao X. J. Org. Chem. 2008; 73: 3159
    Crossref
  • 4 Krusic PJ, Wasserman E, Keizer PN, Morton JR, Preston KF. Science (Washington, D.C.) 1991; 254: 1183
    Crossref
  • 5 Tzirakis MD, Orfanopoulos M. J. Am. Chem. Soc. 2009; 131: 4063
    CrossrefPubMed
  • 6 Zhang T.-H, Lu P, Wang F, Wang G.-W. Org. Biomol. Chem. 2003; 1: 4403
    Crossref
  • 7 Wang G.-W, Li F.-B, Zhang T.-H. Org. Lett. 2006; 8: 1355
    Crossref
  • 8 Li F.-B, Liu T.-X, Huang Y.-S, Wang G.-W. J. Org. Chem. 2009; 74: 7743
  • 9 Li C.-Z, Zhang D.-W, Zhang X.-T, Wu S.-H, Gao X. Org. Biomol. Chem. 2004; 2: 3464
    Crossref
  • 10 Boltalina OV, Darwish AD, Street JM, Taylor R, Wei X.-W. J. Chem. Soc., Perkin Trans. 2 2002; 251
  • 11 Dorozhkin EI, Goryunkov AA, Ioffe IN, Avdoshenko SM, Markov VY, Tamm NB, Ignat’eva DV, Sidorov LN, Troyanov SI. Eur. J. Org. Chem. 2007; 5082
  • 12 Yang W, Zhang J.-M, Lou H, Wang S. Chin. J. Org. Chem. 2004; 24: 231
  • 13 Zhang J.-M, Yang W, He P, Zhu S.-Z. Chin. J. Chem. 2004; 22: 1008
  • 14 Zhang J.-M, Yang W, Wang S, He P, Zhu S.-Z. Synth. Commun. 2005; 35: 89
    Crossref
  • 15 Wang S, Zhang J.-M, Song L.-P, Jiang H, Zhu S.-Z. J. Fluorine Chem. 2005; 126: 349
    Crossref
  • 16 Wang S, He P, Zhang J.-M, Jiang H, Zhu S.-Z. Synth. Commun. 2005; 35: 1803
    Crossref
  • 17 Wang S, Jiang H, Lv X.-Y, Song L.-P, Zhang J.-M. Chin. J. Org. Chem. 2006; 26: 168
  • 18 Jiang H, Zhang J.-M, Du W.-Q, Zhu S.-Z. Chin. J. Chem. 2007; 25: 86
    Crossref
  • 19 Jiang, H.; Wang, S.; Lv, X.-Y.; Song, L.-P.; Zhang, J.-M. 17th International Symposium on Fluorine Chemistry, Shanghai, P. R. of China, 24–29 July 2005; 164
    • 20a Wang G.-W, Zhang T.-H, Cheng X, Wang F. Org. Biomol. Chem. 2004; 2: 1160
      Crossref
    • 20b Wang G.-W, Li F.-B. Org. Biomol. Chem. 2005; 3: 794
    • 20c Chen Z.-X, Wang G.-W. J. Org. Chem. 2005; 70: 2380
      Crossref
    • 20d Cheng X, Wang G.-W, Murata Y, Komatsu K. Chin. Chem. Lett. 2005; 16: 1327
    • 20e Wang G.-W, Yang H.-T, Miao C.-B, Xu Y, Liu F. Org. Biomol. Chem. 2006; 4: 2595
      Crossref
    • 20f Wang G.-W, Wang C.-Z, Zhu S.-E, Murata Y. Chem. Commun. 2011; 47: 6111
      Crossref
    • 20g Wang G.-W, Wang C.-Z, Zou J.-P. J. Org. Chem. 2011; 76: 6088
      Crossref
    • 20h Liu T.-X, Li F.-B, Wang G.-W. Org. Lett. 2011; 13: 6130
      Crossref
  • 21 Li F.-B, Zhu S.-E, Wang G.-W. Chin. Sci. Bull. 2010; 55: 2909
    Crossref