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

Abstract

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.

Keywords:

• Ceric ammonium nitrate
• diquinone
• oxidation
• quinone

Acknowledgements

A fellowship from the Burroughs-Wellcome Fund administered by the ECU Department of Chemistry is gratefully acknowledged.

Disclosure statement

The authors report there are no competing interests to declare.