Issue 23, 2004
From the journal:

Organic & Biomolecular Chemistry

Manganese(iii) acetate-mediated free radical reactions of [60]fullerene with β-dicarbonyl compounds

Changzhi Li,a   Danwei Zhang,a   Xiaotong Zhang,a   Shihui Wua  and  Xiang Gao*a  

* Corresponding authors

a Department of Chemistry, Fudan University, Shanghai, PR China
E-mail: gaoxiang@fudan.edu.cn

Abstract

[60]Fullerene reacted with various β-dicarbonyl compounds in the presence of Mn(OAc)3·2H2O to generate dihydrofuran-fused [60]fullerene derivatives or 1,4-bisadducts. Dihydrofuran-fused [60]fullerene derivatives 2 could be formed by treatment of α-unsubstituted β-diketones 1a–e or β-ketoesters 1f and 1g with [60]fullerene in refluxing chlorobenzene in the presence of Mn(III). Solvent-participated unsymmetrical 1,4-bisadducts 3 were obtained through the reaction of [60]fullerene with dimethyl malonate 1h or α-substituted β-dicarbonyl compounds 1i–1n in toluene. A possible reaction mechanism for the formation of different fullerene derivatives is proposed.

Graphical abstract: Manganese(iii) acetate-mediated free radical reactions of [60]fullerene with β-dicarbonyl compounds

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Article information

DOI
https://doi.org/10.1039/B411862F
Article type
Paper
Submitted
03 Aug 2004
Accepted
27 Sep 2004
First published
20 Oct 2004

Org. Biomol. Chem., 2004,2, 3464-3469

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Manganese(III) acetate-mediated free radical reactions of [60]fullerene with β-dicarbonyl compounds

C. Li, D. Zhang, X. Zhang, S. Wu and X. Gao, Org. Biomol. Chem., 2004, 2, 3464 DOI: 10.1039/B411862F

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