Preparation of a C70 Bis-heterocyclic Derivative with High Chemio- and Regioselectivity

C70 bis-heterocyclic derivative (1) bearing one oxazoline ring and one imidazoline ring with the 2 o’clock configuration is obtained with high chemio- and regioselectivity via the reaction of C70 with hydroxide and benzonitrile quenched with I2. Further study with benzylation experiment and theoretical calculations indicate that the oxazoline ring is the one first formed on the C70 cage, while the imidazoline ring is the one formed after the addition of I2 via a radical coupling reaction mechanism.