Reaction of [60]fullerene with free radicals generated from active methylene compounds by manganese(III) acetate dihydrate.
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 the addition of free radicals from the active methylene compounds generated by Mn(OAc)3.2H2O.
Zhang
Ting-Hu
TH
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
Lu
Ping
P
Wang
Fan
F
Wang
Guan-Wu
GW
D000085:Acetates / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D005609:Free Radicals / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry; D008345:Manganese / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry*; D008956:Models, Chemical; D013997:Time Factors
D000085:Acetates; D005609:Free Radicals; D037741:Fullerenes; D008314:Malonates; D008345:Manganese; C069837:fullerene C60; D008697:Methane