Products from the reaction of C60F18 with sarcosine and aldehydes: the Prato reaction

Various pyrrolidinofullerenes (both mono- and bis-addition products) have been isolated from the reaction between toluene solutions of C60F18, N-methyl-2-aminoethanoic acid (sarcosine) and either formaldehyde or benzaldehyde. Both mono- and bis-addition products were obtained and either partially of fully characterised. The main mono-addition product from the reaction with formaldehyde was also obtained from reactions with the other aldehydes, indicating that formaldehyde may be present in sarcosine, or generated from it through in situ oxidation by the fullerene. The main mono-addition product from reaction of C60F18 with toluene solutions of sarcosine and benzaldehyde was obtained also in the absence of benzaldehyde. This anomaly was traced to the presence of benzaldehyde (0.05%) in HPLC grade toluene, which may be increased by oxidation of toluene during the reaction conditions.