Oxygenation of Benzyldimethylamine by Singlet Oxygen. Products and Mechanism

A product study of the reaction of benzyldimethylamine (<b>1</b>) with thermally and photochemically generated <sup>1</sup>O<sub>2</sub> in MeCN was carried out. Benzaldehyde and<i> N</i>-benzyl-<i>N</i>-methylformamide are the reaction products, oxygenation representing ca. 9% of the overall quenching of <sup>1</sup>O<sub>2</sub> by <b>1</b>. 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.