The reactions of tetrachloro- and tetrabromo-o-benzoquinone with acyclic dienes
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 1423-1429
- https://doi.org/10.1039/j39710001423
Abstract
The formation of spirodihydropyrans by the cycloaddition of acyclic dienes to one of the carbonyl groups in tetrachloro- or tetrabromo-o-benzoquinone is reported. The products are Claisen rearrangement intermediates, and are thermally converted into benzodioxans. The spirodihydropyrans are shown to react further with dienes to give 2 : 1 adducts. In some cases these adducts undergo Cope rearrangements, the results of which establish their structures.Keywords
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