The 2- or 6-(α-Hydroxyalkyl- and α-Oxoalkyl)-5,8-dimethoxy-1,4-naphthoquinones from the Oxidative Demethylation of 2-(α-Hydroxyalkyl- and α-Oxoalkyl)-1,4,5,8-tetramethoxynaphthalenes with Cerium(IV) Ammonium Nitrate, and the Further Demethylations to Naphthazarins
- 1 June 1988
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 61 (6) , 2039-2045
- https://doi.org/10.1246/bcsj.61.2039
Abstract
Oxidative demethylation of 2-(α-hydroxyalkyl- and α-oxoalkyl)-1,4,5,8-tetramethoxynaphthalene with (NH4)2Ce(NO3)6 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%HNO3 reagent, while the latter isomers needed AlCl3 as the demethylation reagent. Some comments regarding the mechanism of these oxidative demethylations with (NH4)2Ce(NO3)6 are given.Keywords
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