Diels-Alder reactions in high temperature water

CHED 380

Sarah M. Tauer, gron@hendrix.edu and Liz Gron, gron@hendrix.edu. Department of Chemistry, Hendrix College, 1600 Washington Avenue, Conway, AR 72032
The Diels-Alder (DA) reaction, a powerful tool for creating six-membered ring systems, is significantly accelerated in water. However; solubility limitations diminish the utility of this solvent. We are exploiting the physical properties of high temperature water (T > 100 °C and P > 200 bar) to create a novel solvent replacement option. Manipulation of the temperature and pressure reduces the dielectric constant and other underlying physical properties of water to make it a reasonable solvent for Diels-Alder reactions.