Bridged Synthons from Tetrabromocyclopropene: Studies on the Rearrangement of the Primary Diels−Alder Adduct with 2,5-Dimethylfuran
- 30 December 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (2), 570-572
- https://doi.org/10.1021/jo0352631
Abstract
The reaction of tetrabromocyclopropene and furan leads directly to 8-oxabicyclo[3.2.1]octadiene derivatives. It has been proposed that this involves an initial Diels−Alder reaction followed by rearrangement of the primary adduct. We have, for the first time, isolated a primary adduct and established through X-ray crystallographic analysis that the adduct is the product of an exo-selective addition. Kinetic studies suggest the intermediacy of charged intermediates during the rearrangement.Keywords
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