Reductive benzylation of C60 imidazoline with a bulky addend.

Reductive benzylation of C60 imidazoline with a bulky addend affords two 1,2,3,16-adducts (2 and 4) and one 1,2,3,4-adduct (3). Experimental and computational results indicate that the sterically favored 2 is more stable than the electronically favored 3. However, an opposite stability order is shown for the dianions of 2 and 3.