Journal article
Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 3. 3-Methoxyfuran and methoxydehydrobenzenes and the chemistry of their adducts
Journal of the Chemical Society, Perkin Transactions 1, (6), pp.1589-1600
1991
Abstract
The cycloadditions of methoxydehydrobenzenes containing a 3-methoxy group and 3-methoxyfuran are highly regioselective. The adducts, 1,4-dihydro-2-methoxy-1,4-epoxynaphthalenes, undergo mild acid-catalysed hydrolysis providing, first, an isolable 1,2,3,4-tetrahydro-2-methoxy-1,4-epoxy-naphthalen-2-ol, and then a 3,4-dihydro-1,4-epoxynaphthalen-2(1H)-one. The chemistry of these ketones is explored. One of them, 3,4-dihydro-5-methoxy-1,4-epoxynaphthalen-2(1H)-one, readily undergoes catalytic reduction to yield the hexahydro-1,4-epoxynaphthalene-2,5(1H,4aH)dione. The X-ray molecular structure of this dione and of the 2-monobrosyl ester of the derived diol are reported. Treatment of the above adducts with trifluoroacetic acid and acetic anhydride provides a convenient synthesis of 1-acetoxy-2-methoxynaphthalenes.
Details
- Title
- Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 3. 3-Methoxyfuran and methoxydehydrobenzenes and the chemistry of their adducts
- Authors/Creators
- R.W. Baker (Author/Creator)T.M. Baker (Author/Creator)A.A. Birkbeck (Author/Creator)R.G.F. Giles (Author/Creator)M.V. Sargent (Author/Creator)B.W. Skelton (Author/Creator)A.H. White (Author/Creator)
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 1, (6), pp.1589-1600
- Publisher
- Chemical Society
- Identifiers
- 991005543297707891
- Murdoch Affiliation
- School of Mathematical and Physical Sciences
- Language
- English
- Resource Type
- Journal article
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