Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012; 44(15): 2347-2352
DOI: 10.1055/s-0031-1290409
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
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.
Key words
C60-fused lactones - fluorinated phenylacetic acids - manganese(III) acetate - stereoisomersSupporting 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
- 1b Hirsch A. Synthesis 1995; 895
- 1c Diederich F, Thilgen C. Science (Washington, D.C.) 1996; 271: 317
- 1d Thilgen C, Diederich F. Chem. Rev. 2006; 106: 5049
- 2 Tzirakis MD, Orfanopoulos M. Org. Lett. 2008; 10: 873
- 3 Zheng M, Li F.-F, Ni L, Yang W.-W, Gao X. J. Org. Chem. 2008; 73: 3159
- 4 Krusic PJ, Wasserman E, Keizer PN, Morton JR, Preston KF. Science (Washington, D.C.) 1991; 254: 1183
- 5 Tzirakis MD, Orfanopoulos M. J. Am. Chem. Soc. 2009; 131: 4063
- 6 Zhang T.-H, Lu P, Wang F, Wang G.-W. Org. Biomol. Chem. 2003; 1: 4403
- 7 Wang G.-W, Li F.-B, Zhang T.-H. Org. Lett. 2006; 8: 1355
- 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
- 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
- 15 Wang S, Zhang J.-M, Song L.-P, Jiang H, Zhu S.-Z. J. Fluorine Chem. 2005; 126: 349
- 16 Wang S, He P, Zhang J.-M, Jiang H, Zhu S.-Z. Synth. Commun. 2005; 35: 1803
- 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
- 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
- 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
- 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
- 20f Wang G.-W, Wang C.-Z, Zhu S.-E, Murata Y. Chem. Commun. 2011; 47: 6111
- 20g Wang G.-W, Wang C.-Z, Zou J.-P. J. Org. Chem. 2011; 76: 6088
- 20h Liu T.-X, Li F.-B, Wang G.-W. Org. Lett. 2011; 13: 6130
- 21 Li F.-B, Zhu S.-E, Wang G.-W. Chin. Sci. Bull. 2010; 55: 2909