Abstract
Competitive Diels-Alder reactions between ethyl acrylate and 2-hydroxyethyl acrylate (1,3-cyclopentadiene, CH2Cl2, 0°C) in the presence of a variety of Lewis acids indicate that selective complexation of the 2-hydroxyethyl ester can be accomplished, most notably using EtAlCl2. Further Diels-Alder reactions using ethyl 2-hydroxyethyl fumarate support these findings. 13C NMR studies provide direct evidence for the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2.
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