Abstract
The aqueous Diels-Alder reaction between 2-methylfuran and maleic acid in water is 99.9% stereospecific. Addition of heavy but not light atom salts to the retrodiene reaction reduces the degree of stereospecificity significantly. Taking into account the relatively low concentration (3.5–7 M) of heavy atoms, and the rapid fall off of the heavy atom effect with distance, these results show that a large portion, if not all of the Diels Alder occurs via diradical intermediates.
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