This exercise demonstrates an important reaction class (pericyclic reactions) in an alternative reaction medium (water) and shows the benefits (rate enhancement as well as reduced hazard) of using this alternative medium. Reaction between anthracene-9-methanol and N-methylmaleimide in water is complete in one hour and produces a high yield of the Diels-Alder adduct. The exercise provides a good context for discussing the challenges and benefits of using alternative solvents and, in particular, points out the enhancements in reactivity that can be promoted in these media.
Summary prepared July 2006 by James E. Hutchison, Department of Chemistry at the University of Oregon.
McKenzie, L. C.; Huffman, L. M.; Hutchison, J. E. Diels-Alder reaction in water, Department of Chemistry, University of Oregon, manuscript in preparation, 2006