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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

Giles, R.G.F., Sargent, M.V. and Sianipar, H. (1991) Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 1. Reactions of 3-methoxydehydrobenzene and 3-(methoxycarbonyl)-dehydrobenzene with 2-substituted furans. Journal of the Chemical Society, Perkin Transactions 1 (6). p. 1571.

Link to Published Version: http://dx.doi.org/10.1039/P19910001571
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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.

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: Royal Society of Chemistry
Copyright: © 1991 by the Royal Society of Chemistry.
URI: http://researchrepository.murdoch.edu.au/id/eprint/35764
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