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The electronic nature of substituents present in 1,4-dimethoxybenzene derivatives has been found to have a profound effect on whether or not such substrates can be oxidized to diquinones using ceric ammonium nitrate (CAN). In particular, there appears to be a correlation between the Hammett σ p  value of a substituent and the yield of the corresponding diquinone obtained upon treatment of the dimethoxybenzene derivative with CAN. This information could aid in the prediction of whether or not a given substrate would be expected to produce a diquinone upon such oxidation.

Electronic effects in the oxidation of 1,4-Dimethoxybenzene derivatives with ceric ammonium nitrate