Discovery and Mechanistic Study of a Totally Organic C (aryl) -C (alkyl) Oxygen Insertion Reaction.

We report an unprecedented photochemical oxygen insertion reaction into an aromatic quinone methide. Insertion happens specifically within a C-(aryl)- C-(alkyl) bond, whereas the quinone methide moiety remains intact itself. Detailed mechanistic studies, supported by DFT calculations, support a pathway in which the p-QM plays a pivotal activating role.