Ring-opening metathesis polymerization, or ROMP, is a reaction driven by the favorability of relieving ring strain which results from the opening of cyclic structures containing an olefin. While ROMP has been used extensively to synthesize various types of polymers, there has been little exploration of cyclic alkenes containing sulfone appendages. Vinyl sulfonyl norbornene monomers were synthesized through Diels-Alder reactions. The potential ROMP monomers were selected based on results from an initial project that examined the viability of using vinyl sulfone derivatives for reversible Diels-Alder dendrimer synthesis. Due to the COVID-19 pandemic, the dendrimer project began with a computational investigation of the reaction between methyl vinyl sulfone and different cyclic dienes such as furan, cyclopentadiene, thiophene and dimethyl fulvene. The changes in enthalpy and free energy for both the overall reactions and transition states were calculated using ab initio calculations performed at the B3LYP/6-31G(d), M062x/6-311G(2d,p), wB97xd/6-311G(2d,p) and CBS-QB3 levels of theory using the software Gaussian16. The generated values indicated that the reactions involving furan and dimethyl fulvene could be reversible under mild conditions, although synthetic work demonstrated that this was not the case. Consequently, the focus of the project was shifted to polymer synthesis. 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. The monomers were then reacted to form polymers through ROMP using a third generation Grubbs catalyst. The polymers were analyzed using gel permeation chromatography (GPC). This study has shown that Diels-Alder adducts can be formed from reacting a diene with different vinyl-sulfone derivatives to create ideal monomers for ROMP, providing a straightforward means of synthesizing new sulfone functionalized polymers. The initial GPC results suggest that a number of these polymerizations are well-controlled and could provide the basis for materials with new and exciting physical properties in the future.