The key role of aromaticity in the structure and reactivity of C60 and endohedral metallofullerenes

Abstract

In this review, we show that the local aromaticity of C 60 and endohedral metallofullerenes (EMFs) is a key factor to understand and predict their structure and reactivity. We report recent examples provided by our group that highlight the importance of aromaticity in C 60 and EMFs. First example discusses the regioselectivity of Diels-Alder reactions in reduced C 60 ; the second one analyzes how aromaticity stabilizes the most suitable hosting cages in EMFs; the third one determines the effect of aromaticity in the relative abundances of EMFs; the fourth one shows a relationship between aromaticity and the stability of EMF adducts formed in Bingel-Hirsch (BH) reactions; and the last one proposes structural criteria to predict the regioselectivity in BH reactions based on the local aromaticity of EMFs