Iodo-controlled selective formation of pyrrolidino[60]fullerene and aziridino[60]fullerene from the reaction between C60 and amino acid esters

The reaction between glycine methyl ester and C-60 can be effectively controlled by different iodo-reagents. Addition of DIB ((diacetoxyiodo)benzene) yields the 2,5-bismethoxycarbonyl pyrrolidino[60]fullerene under ultrasonic irradiation; whereas addition of DIB-iodine results in the N-methoxycarbonylmethyl aziridino [60] fullerene under ultrasonic irradiation. The reaction of sarcosine methyl ester with C-60 is similar to that of glycine methyl ester under these two conditions. Addition of just iodine to a mixture of sarcosine methyl ester and C-60 affords the tetra(amino) [60] fullerene epoxide C-60(O)((Me)NCH2COOMe)(4). Possible mechanisms are discussed.