The [2+1] Cycloaddition of Singlet Oxycarbonylnitrenes to C60

Semiempirical and density functional calculations have been carried out to discuss the origin of the closed 5,6]-aza-bridged adduct obtained as a minor product in the reaction of singlet nitrenes with C₆₀. The results indicated that the most likely source is the direct addition of singlet nitrenes to a 5,6]-bond of C₆₀, in contradiction to the common belief that the 5,6]-bonds are not attacked in cycloaddition reactions to C₆₀.Electronic Supplementary Material available.