Abstract: Ring-opening metathesis polymerization, or ROMP, is a reaction driven by the favorability of relieving ring strain which results in the opening of cyclic structures that contain an alkene. While ROMP has been used extensively to synthesize various types of polymers, there has been little exploration of cyclic alkenes containing vinyl sulfone derivatives. For this project, vinyl sulfonyl norbornene monomers were synthesized through Diels-Alder reactions. Cyclopentadiene and furan were used as dienes and reacted with numerous dienophiles: isopropoxy vinyl sulfone, n-butoxy vinyl sulfone, n-hexyloxy vinyl sulfone, ethyl vinyl sulfone, and phenyl vinyl sulfone. The synthesized structures were analyzed through 1H NMR and 2D COSY NMR. Relative Gibbs transition state and reaction free energies were calculated using Gaussian16 optimizations performed at the M062x/6-311G(2d,p) level of theory. In the future, each of the norbornene products synthesized will be reduced to their thioether and sulfoxide forms. The resulting products will be used as monomers for ROMP to form various polymers, which are expected to have new and exciting properties.
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