Influence of the concentration in the anodic oxidations of α-chloro-ethylbenzene or toluene in acetonitrile

In the anodic oxidation of α-chloro-ethylbenzene the reaction course depends on the substrate concentration conditions. When the starting compound is added drop wise into the anolyte N-(2-acetylphenyl)acetamide (1) is obtained in good yield, however 2,6-dimethyl-4-phenylpyrimidine (2) is the main product when the electrolysis starts with the whole substrate in the cell. Electrolysis where toluene is dropped into the anodic compartment afforded 2,6-dimethyl-4-phenylpyridine-3,5-dicarbonitrile (3) via a radical process.