Kinetics and mechanism of the reaction of benzyl bromide with copper in dimethylacetamide in the presence of oxygen

The reaction of copper metal with benzyl bromide in dimethylacetamide in the presence of oxygen has been studied. Oxidative dissolution of copper follows the single-electron transfer mechanism with formation of benzaldehyde, benzyl alcohols, and copper(II) coordination compounds. The kinetic and thermodynamic parameters of the process have been determined by resistometry. Intermediately formed species have been identified and quantitated, and the reaction stereochemistry has been studied. The reaction mechanism is discussed.