Microwave and Neat Synthesis of 7-Oxanorbornene Derivatives for Organic Chemistry Teaching Lab: A Comparison Study

This presentation was given at the 255th ACS National Meeting & Exposition. Abstracts In response to a review of our degree programs by the American Chemical Society Committee on Professional Training (ACS CPT) and the newly revised guidelines for ACS-certified degrees that mandate inclusion of polymer concepts, the chemistry and biochemistry faculty at Armstrong State University (ASU) in Savannah, GA developed a new model to weave themes of synthetic polymers, biological macromolecules, and supramolecular aggregates throughout our curriculum. For example, we have developed two methods to synthesize 7-oxanorbornene derivatives for the Organic Chemistry teaching laboratory to be used as monomers for ROMP (ring-opening metathesis polymerization) reactions in the Inorganic Chemistry teaching laboratory. The general reaction scheme involves a Diels-Alder reaction of furan and maleic anhydride, followed by ring opening of the cyclic anhydride via Fischer TransEsterification. Unfortunately, the reported procedure requires long reaction times and/or high temperatures. The first method uses microwave synthesis, while the other is a neat, “green”, one-pot synthesis. In addition, we began examining various alcohols in the trans-esterification step to gauge the applicability of this reaction to provide a collection of sterically-diverse monomers for the ROMP reaction. These experiments have already been conducted by students in organic chemistry and the monomers have been polymerized by students in the inorganic chemistry laboratory reactions using ROMP techniques. We provide here a comparison of the two reaction methods including their benefits and detriments. The two methods can provide interested stakeholders a means to incorporate the experiment into their curriculum regardless of their resources