Addition Reaction of Benzyne to C60

Abstract
Benzyne generated by the reaction of 2-aminobenzoic acid and pentyl nitrite in a refluxing benzene was found to add to C60 in good yield. The reaction products were separated by HPLC to give C60(C6H4), C60(C6H4)2, C60(C6H4)3, and C60(C6H4)4, which were confirmed by mass spectra. 1H NMR spectrum of C60(C6H4) is consistent with the structure of mono-addition product, whereas those of C60(C6H4)2, C60(C6H4)3, and C60(C6H4)4 indicate that they consist of the corresponding mixtures of isomers.