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. This resulted in good yields of endo and exo 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. Attempts to increase the reaction rates by heating above room temperature increased the exo:endo ratios significantly. It was then discovered that heating pure endo isomer yields a mixture of both endo and exo isomers, where the isomerization yields predominately the exo isomer.

Endo/exo thermal isomerization of a green Diels-Alder adduct

249th National Meeting (2015)

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