The 2- or 6-(.ALPHA.-hydroxyalkyl- and .ALPHA.-oxoalkyl)-5,8-dimethoxy-1,4-naphthoquinones from the oxidative demethylation of 2-(.ALPHA.-hydroxyalkyl- and .ALPHA.-oxoalkyl)-1,4,5,8-tetramethoxynaphthalenes with cerium(IV) ammonium nitrate, and the furthe
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Oxidative demethylation of 2-(α-hydroxyalkyl- and α-oxoalkyl)-1,4,5,8-tetramethoxynaphthalene with (NH<SUB>4</SUB>)<SUB>2</SUB>Ce(NO<SUB>3</SUB>)<SUB>6</SUB> gave two isomeric dimethoxynaphthoquinones: 2-substituted and 6-substituted 5,8-dimethoxy-1,4-naphthoquinones. Further demethylations of the former isomers to the corresponding dihydroxynaphthoquinones required an AgO–40%HNO<SUB>3</SUB> reagent, while the latter isomers needed AlCl<SUB>3</SUB> as the demethylation reagent. Some comments regarding the mechanism of these oxidative demethylations with (NH<SUB>4</SUB>)<SUB>2</SUB>Ce(NO<SUB>3</SUB>)<SUB>6</SUB> are given.
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