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47.1.3.1.3.1.4 Variation 4: In Supercritical Water

DOI: 10.1055/sos-SD-047-00252

Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L.Science of Synthesis, (201047701.

The first report of a DielsAlder reaction performed in supercritical water appeared in 1997,[‌517‌] and it showed that cycloadditions carried out under these conditions are generally fast, and may occur in good yields (Scheme 138). Thus, cyclohexenecarbonitriles are obtained in a few minutes from suitable starting materials. Similarly, the cycloaddition of ethyl acrylate to cyclopentadiene is complete within 2hours in supercritical water, while in water at 50°C 8hours is required. The configuration of the dienophile is sometimes crucial for the success of the reaction; for example, while diethyl maleate reacts with cyclopentadiene within an hour at 337°C to afford the required adduct in 86% yield, under the same reaction conditions its diastereomer diethyl fumarate gives only 10% of the corresponding adduct.[‌517‌]

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