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Synfacts 2006(10): 1014-1014  
DOI: 10.1055/s-2006-949362
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic 1,4-Substitution of Fullerene Epoxides

Contributor(s): Timothy M. Swager, Eric L. Dane
Y. Tajima*, T. Hara, T. Honma, S. Matsumoto, K. Takeuchi
RIKEN and Saitama University, Japan
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

A simple and robust procedure is reported for regioselectively substituting C60-epoxides with nucleophilic aromatic compounds. The authors suggest that steric interactions direct the formation of the 1,4-product, instead of the 1,2-product, through an SN1-type allylic substitution of the hydroxyl group formed by the initial epoxide opening.