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Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 1. Reactions of 3-methoxydehydrobenzene and 3-(methoxycarbonyl)-dehydrobenzene with 2-substituted furans
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Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 1. Reactions of 3-methoxydehydrobenzene and 3-(methoxycarbonyl)-dehydrobenzene with 2-substituted furans

R.G.F. Giles, M.V. Sargent and H. Sianipar
Journal of the Chemical Society, Perkin Transactions 1, (6)
1991
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Abstract

The isomer ratios for the cycloadducts obtained for the reaction of 3-methoxydehydrobenzene, generated from 2-amino-6-methoxybenzoic acid by aprotic diazotization, or from 2-bromo-3- methoxyphenyl toluene-p-sulphonate by treatment with butyllithium, and for the reaction of 3-(methoxycarbonyl)dehydrobenzene, generated from 2-amino-6-(methoxycarbonyl)benzoic acid by aprotic diazotization, with seven 2-substituted furans are recorded. These results are discussed in terms of an asynchronous, concerted, biradicaloid reaction pathway.

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