The Diels-Alder reaction is one of the most important and widely studied reactions in organic chemistry, and is usually taught and performed in the second-semester of organic chemistry courses. Therefore, a variety of different Diels-Alder experiments that can be used in teaching labs is necessary. Despite the innumerable possible diene-dienophile combinations, very few are actually used for experiments in organic chemistry teaching labs. The reaction of α-phellandrene 1 and p-benzoquinone 2 to produce adduct 3 reported by Diels and Alder in 1928 is an overlooked example that can be considered for this educational purpose. Our work investigated the effects of solvents and other variables on the kinetics of this reaction by refluxing 1 and 2 in various solvents and observing precipitated yields from cooling the reaction solution and collecting the product using vacuum filtration. The primary goal was to achieve a reflux time of &lt;1 h while obtaining a good yield. Adduct 3 can also be used to synthesize 4, the monomer of a polymer used in organic luminescence materials, which may allow this reaction to be used in multistep synthesis projects that can be completed in an upper level polymer chemistry course. This work is still in progress and hence there are no conclusive results at this time.

Diels-Alder reaction of α-phellandrene and p-benzoquinone as an experiment for the organic chemistry teaching lab and subsequent adduct polymerization

255th National Meeting (2018)

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