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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 11
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Original Articles

Solvent‐Free Reactions of Fullerenes with Diethyl Bromomalonate in the Presence of Inorganic Bases Under High‐Speed Vibration Milling Conditions

Ru‐Fang Peng# Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China
,
Guan‐Wu Wang Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China; State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, P.R. ChinaCorrespondence[email protected]
,
Ye‐Bing Shen Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China
,
Yu‐Jin Li Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China; State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, P.R. China
,
Ting‐Hu Zhang Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China
,
You‐Cheng Liu Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China; State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, P.R. China
,
Yasujiro Murata Institute for Chemical Research, Kyoto University, Uji, Kyoto, Japan
&
Koichi Komatsu Institute for Chemical Research, Kyoto University, Uji, Kyoto, Japan
 show all
Pages 2117-2126 | Received 30 Sep 2003, Published online: 20 Aug 2006
 
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Abstract

Solvent‐free reactions of C60 and C70 with diethyl bromomalonate in the presence of various inorganic bases were investigated under the high‐speed vibration milling (HSVM) conditions, and are shown to give methanofullerenes 1 and 2 in good to excellent yields based on consumed fullerenes. Several weak inorganic bases were found to be quite effective in promoting the solvent‐free mechanochemical Bingel reactions of C60 and C70 under the HSVM conditions. Among the studied bases, sodium acetate gave the highest yield of monoadducts, while potassium carbonate afforded a considerable amount of bisadducts for both C60 and C70.

#Visiting Scholar from College of Material Sciences, Southwest University of Science and Technology.

Acknowledgments

We are grateful for financial support from the National Science Fund for Distinguished Young Scholars (21025205), Hundred Talents Program of the Chineese Academy of Sciences, Anhui Provincial Natural Science Foundation (00045306), and Anhui Provincial Bureau of Personnel Affairs (2001Z019).

Notes

#Visiting Scholar from College of Material Sciences, Southwest University of Science and Technology.

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