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Plastics are widely used due to their incredible versatility and ease of manufacturing, but the polymers they are made from do not easily degrade, making recycling ineffective for most plastics. A current branch of organic chemistry research studies “self-destructive” polymers that can be broken down and reconstructed in a closed-loop cycle, hence decreasing the amount of waste produced. My research was focused specifically on investigating poly(glyoxylate imines) as potential self-destructive polymers. I prepared a number of potential glyoxylate imine monomers by reacting ethyl glyoxylate with amines. Attempted cationic and anionic polymerizations of these monomers were unsuccessful, likely due to challenges associated with purifying the monomers or due to the inherent low reactivity of the C=N bond of some glyoxylate imine derivatives. Further investigations into both monomer purification and polymerization will advance the understanding of the glyoxylate imine structure in polymer chemistry.