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

Shaohua Huang; Xiaobing Yang; Xiang Zhang; Xiangqing Hu; Liangbing Gan; Shiwei Zhang

doi:10.1055/s-2006-932462

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Synlett 2006(8): 1266-1268
DOI: 10.1055/s-2006-932462

LETTER

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

Shaohua Huang^a, Xiaobing Yang^a,b, Xiang Zhang^a, Xiangqing Hu^a, 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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Publication History

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

Abstract
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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

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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 C_86.5H₄₉ClO₉, 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 MoK_α-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].