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Synlett 2006(8): 1266-1268  
DOI: 10.1055/s-2006-932462
LETTER
© Georg Thieme Verlag Stuttgart · New York

Preparation of Covalent-Bound Iodofullerene through Selective Opening of Fullerene Epoxide To Form Halohydrin Fullerene Derivatives

Shaohua Huanga, Xiaobing Yanga,b, Xiang Zhanga, Xiangqing Hua, Liangbing Gan*a,c, Shiwei Zhang*d
a Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China
b Beijing Institute of Pharmaceutical Chemistry, P.O. Box 925 (West Building), Beijing 100083, P. R. of China
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
d State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Beijing 100871, P. R. of China
e-Mail: gan@pku.edu.cn;
Further Information

Publication History

Received 1 November 2005
Publication Date:
10 March 2006 (online)

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Abstract

The epoxy moiety in a fullerene mixed peroxide can be opened regioselectively by various Lewis acids to form halohydrin fullerene derivatives. The first iodofullerene was obtained by treating the fullerene epoxide with triphenylphosphine and iodine. A single-crystal structure of the chlorohydrin derivative supports the results.

Key words

fullerene - halohydrin - epoxides - peroxide - Lewis acid

    References and Notes

  • 1a Hirsch A. The Chemistry of Fullerenes   Thieme Verlag; Stuttgart: 1994. 
    Google Scholar
  • 1b Hirsch A. Brettreich M. Fullerenes: Chemistry and Reactions   Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 1c Taylor R. Lecture Notes on Fullerene Chemistry   Imperial College Press; London: 1999. 
    Google Scholar
  • 2a Taylor R. Walton DRM. Nature (London)  1993,  363:  685 
    CrossrefGoogle Scholar
  • 2b Taylor R. Chem. Eur. J.  2001,  7:  4075 
    CrossrefGoogle Scholar
  • 2c Troyanov SI. Troshin PA. Boltalina OV. Ioffe IN. Sidorov LN. Kemnitz E. Angew. Chem. Int. Ed.  2001,  40:  2285 
    CrossrefGoogle Scholar
  • 2d Troyanov SI. Shustova NB. Popov AA. Sidorov LN. Kemnitz E. Angew. Chem. Int. Ed.  2005,  44:  432 ; and references cited therein
    CrossrefGoogle Scholar
  • 3a Zhu Q. Cox DE. Fisher JE. Kniaz K. McGhie AR. Zhou O. Nature (London)  1992,  355:  712 
    CrossrefGoogle Scholar
  • 3b Zenner T. Zabei H. J. Phys. Chem.  1993,  97:  8690 
    CrossrefGoogle Scholar
  • 4 Kissell K. Hartman K. der Heide PV. Wilson LJ. J. Phys. Chem. B  2005,  109:  5482 
    CrossrefGoogle Scholar
  • 5 Li Y. Zhang X. Li Q. Li W. J. Radioanal. Nucl. Chem.  2001,  250:  363 
    CrossrefGoogle Scholar
  • 6 Wharton T. Wilson LJ. Bioorg. Med. Chem.  2002,  10:  3545 
    CrossrefGoogle Scholar
  • 7a Gan LB. Huang SH. Zhang X. Zhang AX. Cheng BC. Cheng H. Li XL. Shang G. J. Am. Chem. Soc.  2002,  124:  13384 
    CrossrefGoogle Scholar
  • 7b Huang SH. Xiao Z. Wang FD. Gan LB. Zhang X. Hu XQ. Zhang SW. Lu MJ. Pan JQ. Xu L. J. Org. Chem.  2004,  69:  2442 
    CrossrefGoogle Scholar
  • 7c Huang SH. Xiao Z. Wang FD. Zhou J. Yuan G. Zhang SW. Chen ZF. Thiel W. Schleyer PR. Zhang X. Hu XQ. Chen BC. Gan LB. Chem. Eur. J.  2005,  11:  5449 
    CrossrefGoogle Scholar
  • 9a Palumbo G. Ferreri C. Caputo R. Tetrahedron Lett.  1983,  24:  1307 
    CrossrefGoogle Scholar
  • 9b Caputo R. Chianese M. Ferreri C. Palumbo G. Tetrahedron Lett.  1985,  26:  2011 
    CrossrefGoogle Scholar
  • 10 Cotton FA. Kibala PA. J. Am. Chem. Soc.  1987,  109:  3308 
    CrossrefGoogle Scholar
  • 11 Godfrey SM. Kelly DG. McAuliffe CA. Mackie AG. Pritchard RG. Watson SM. J. Chem. Soc., Chem. Commun.  1991,  17:  1163 
    Google Scholar
8

Single crystals suitable for X-ray diffraction analysis were obtained for 2b by slow evaporation of a toluene solution at 5 °C. Crystal data for 2b C86.5H49ClO9, M = 1267.71, monoclinic, P2 (1)/c, a = 12.749 (3), b = 13.984 (3), c = 33.372 (7) Å, α = 90°, β = 97.35 (3)°, γ = 90°, V = 5901 (2) Å3, T = 293 (2) K, Z = 4, ρ calcd = 1.4427 mg/m3, graphite monochromatized MoKα-radiation, λ = 0.71073 Å, crystal size 0.50 ¥ 0.20 ¥ 0.15 mm3. Data collected on a Rigaku RAXIS RAPID IP diffractometer, 9979 unique reflections (R int = 0.0529). Refinement on F 2, final residuals R1 = 0.0723 for 4561 reflections with I>2sI), wR2 = 0.2122 for all data. CCDC-287295 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/consts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: +44(1223)366033; or e-mail: deposit@ccdc.cam.ac.uk].