Regioselectivity in the reactions of methoxydehydrobenzenes with furans. Part 1. Reactions of 3-methoxydehydrobenzene and 3-(methoxycarbonyl)-dehydrobenzene with 2-substituted furans
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1571-1579
- https://doi.org/10.1039/p19910001571
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.Keywords
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