Oxygenation of Benzyldimethylamine by Singlet Oxygen. Products and Mechanism

A product study of the reaction of benzyldimethylamine (1) with thermally and photochemically generated ¹O₂ in MeCN was carried out. Benzaldehyde and N-benzyl-N-methylformamide are the reaction products, oxygenation representing ca. 9% of the overall quenching of ¹O₂ by 1. The temperature effect and the intermolecular and intramolecular kinetic deuterium isotope effects were also determined. It is suggested that the products derive from an intracomplex hydrogen atom transfer in a reversibly formed charge-transfer complex.