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Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 3. 3-Methoxyfuran and methoxydehydrobenzenes and the chemistry of their adducts

Baker, R.W., Baker, T.M., Birkbeck, A.A., Giles, R.G.F., Sargent, M.V., Skelton, B.W. and White, A.H. (1991) 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.

Link to Published Version: http://dx.doi.org/10.1039/P19910001589
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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.

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: Chemical Society
URI: http://researchrepository.murdoch.edu.au/id/eprint/35773
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