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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;
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Publikationsverlauf

Received 1 November 2005
Publikationsdatum:
10. März 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

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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].