Ketenes offer the potential to functionalize polymers with unprecedented simplicity. The power of ketenes is their dual reactivity, providing functionalization by nucleophilic addition across the C=C bond and crosslinking via dimerization, allowing one to tailor a polymer system to specific applications. The ketene functionality is accessed through heating Meldrum’s acid to > 200 ?C. This high temperature, however, limits the use of ketenes in polymer systems because it will degrade many polymer backbones and disrupt functionalization. To address such issues, we propose to use well-known physical-organic phenomenon to lower the thermolysis temperature of Meldrum’s acid derivatives. In the study, two such derivatives have been made—one containing a triazole and one containing an ether, neighboring the ketene precursor. Nuclear magnetic resonance, infrared spectroscopy, and mass spectroscopy were used to identify each monomer. Then nuclear magnetic resonance and gel permeation chromatography confirmed the synthesis of homopolymers, and thermogravimetric analysis revealed thermolysis temperatures of < 190 ?C. This positive result provides initial evidence of temperature reduction through neighboring group participation, and work toward the synthesis of a library of such monomers will continue.