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

60]Fullerene reacted with various beta-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 alpha-unsubstituted beta-diketones 1a-e or beta-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 alpha-substituted beta-dicarbonyl compounds 1i-1n in toluene. A possible reaction mechanism for the formation of different fullerene derivatives is proposed.