Journal article
The acetylation of naphthoquinones. The synthesis of 3-acetyl-5-methoxy- and 3-acetyl-5,7-dimethoxy-1,4-naphthoquinones
Journal of the Chemical Society, Perkin Transactions 1, pp.1339-1343
1984
Abstract
The conversion of 5-methoxy- and 5,7-dimethoxy-1,4-naphthoquinones into their 3-acetyl derivatives is described. A key step is the Fries rearrangement of 1,5-dimethoxy-4-acetoxynaphthalenes to the corresponding 3-acetyl-4-naphthols with boron trifluoride–diethyl ether. Alternative Fries rearrangement of 1-acetoxy-4-hydroxy-5-methoxynaphthalenes gave the 3-acetylquinols, involving meta migration of the acetyl group. A convenient new synthesis of 2-acetyl-1,4-naphthoquinone is also reported.
Details
- Title
- The acetylation of naphthoquinones. The synthesis of 3-acetyl-5-methoxy- and 3-acetyl-5,7-dimethoxy-1,4-naphthoquinones
- Authors/Creators
- T.A. Chorn (Author/Creator)R.G.F. Giles (Author/Creator)I.R. Green (Author/Creator)V.I. Hugo (Author/Creator)P.R.K. Mitchell (Author/Creator)S.C. Yorke (Author/Creator)
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 1, pp.1339-1343
- Publisher
- Royal Society of Chemistry
- Identifiers
- 991005541144907891
- Copyright
- © 1984 Royal Society of Chemistry
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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