How does the addition method of ceric ammonium nitrate (CAN) affect the quinone/diquinone ratio in the oxidation of 2-benzyl-1,4-dimethoxybenzene derivatives?

Label:chem

Topic
The oxidation of 1,4-dimethoxybenzene derivatives with CAN can produce quinones or diquinones depending on the reaction conditions.
Answer
A study found that the traditional addition of CAN to the arene solution in acetonitrile favors quinone formation, yielding compounds 4a and 4b with higher percentages (69% and 78%, respectively). In contrast, the inverse addition of CAN (adding the arene solution to an aqueous CAN solution) favors diquinone formation, yielding compounds 5a and 5b with very high yields (84% and 88%, respectively). This difference is attributed to the solubility of the arene substrates in water, which affects the aggregation and subsequent oxidation pathway.
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