While [60]fullerene is known to readily react with nucleophiles, there are far fewer examples of successful reactions involving electrophilic reagents. An early report by Olah and co-workers suggested that aromatics could be addended to [60]fullerene under Friedel-Crafts type conditions[1]. The work has been largely ignored as it leads to a complex mixture of products with no noticeable regioselectivity. In an effort to better understand the arylation of [60]fullerene under Friedel-Crafts conditions, alkyl substituted benzenes and a number of different acenes have been reacted with [60]fullerene in the presence of AlCl3. Characterization of products by Matrix Assisted Laser Desorption Ionization (MALDI) mass spectrometry reveals an interesting fragmentation pattern in which the aryl substituents readily cleave leaving behind [60]fullerene-bound hydrogen atoms.

[1] Olah, G.; Bucsi, I.; Lambert, C.; Aniszfeld, R.; Trivedi, N.; Sensharma, D.; Prakash, G.K.; J. Am. Chem. Soc. 1991, 113, 9387-9388.