Green chemistry topics are important additions to subjects normally offered at any level of chemistry education. As part of a continuing effort to further green the organic chemistry laboratory curriculum, aqueous and solventless Diels-Alder reactions between 2-furfuryl alcohol and maleimide were developed and resulted in good yields of <i>endo</i> and <i>exo</i> 3a,4,7,7a-tetrahydro-4-(hydroxymethyl)-4,7-epoxy-1H-isoindole-1,3(2H)-dione at room temperature and atmospheric pressure in the hands of students during a single four-hour laboratory period. The enhanced reaction rate observed for the reaction between 2-furfurol and maleimide when compared to reaction rates for reactions between other furans and maleimide suggests the assistance of intermolecular hydrogen bonding. The kinetic parameters for Diels-Alder reactions between several 2-substituted furans and maleimide will be compared to further understand possible assistance by intermolecular hydrogen bonding.

Kinetic study of a green Diels-Alder reaction between 2-furfurol and maleimide

251st National Meeting (2016)

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