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Issue 24, 2003
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Reaction of [60]fullerene with free radicals generated from active methylene compounds by manganese(III) acetate dihydrate

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Abstract

The reaction of [60]fullerene with dimethyl malonate and diethyl malonate in the presence of manganese(III) acetate dihydrate (Mn(OAc)3·2H2O) for 20 min afforded singly bonded [60]fullerene dimers 1a and 1b in a 1,4-addition pattern. When the reaction time was extended to 1 h, 1,4-bisadducts 2a and 2b were obtained. Unsymmetrical 1,4-adduct 5 and C2 symmetrical 1,16-bisadduct 6 were obtained when diethyl bromomalonate was used as the active methylene compound. Reaction of [60]fullerene with malononitrile and ethyl cyanoacetate with the aid of Mn(OAc)3·2H2O produced methanofullerenes 7 and 8. It is proposed that all these products were formed via the addition of free radicals from the active methylene compounds generated by Mn(OAc)3·2H2O.

Graphical abstract: Reaction of [60]fullerene with free radicals generated from active methylene compounds by manganese(iii) acetate dihydrate

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Publication details

The article was received on 19 Aug 2003, accepted on 10 Oct 2003 and first published on 03 Nov 2003


Article type: Paper
DOI: 10.1039/B309939C
Citation: Org. Biomol. Chem., 2003,1, 4403-4407
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    Reaction of [60]fullerene with free radicals generated from active methylene compounds by manganese(III) acetate dihydrate

    T. Zhang, P. Lu, F. Wang and G. Wang, Org. Biomol. Chem., 2003, 1, 4403
    DOI: 10.1039/B309939C

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