Electrochemical functionalization of linear alkylbenzenes in acetic acid

Electrochemical oxidation of linear ethylbenzene, phenylhexane, phenylheptane, phenyloctane, and phenylnonane in acetic acid was followed by electroanalytical techniques. Electrochemical parameters were determined and a correlation between these values and the side chain length was established. The side chain substitution of phenylhexane is the route followed when electrolyses are performed at the first voltammetric wave, while a combination of processes occurs (side chain substitution and aromatic ring substitution) when electrolyses are performed at potentials on the second voltammetric wave. For alkylbenzenes with chains containing more than six atoms of carbon, the main product exhibited a ring substitution, while those with shorter chains are nonspecifically functionalized, either on the side chain or on the aromatic ring.