Preparation of a C-70 Bis-heterocyclic Derivative with High Chemio- and Regioselectivity

摘要

C-70 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 C-70 with hydroxide and benzonitrile quenched with I-2. Further study with benzylation experiment and theoretical calculations indicate that the oxazoline ring is the one first formed on the C-70 cage, while the imidazoline ring is the one formed after the addition of I-2 via a radical coupling reaction mechanism.