Notably, the Sterimol B5 and the MV Vbur-min conformers were found to be collinear, and the same parameters derived from other conformers (i.e., low E, min, and max values) do not perform nearly as well (Supporting Information Section 13). Overall, these data suggest that the overall size and shape of the monomer has a significant impact on polymerization kinetics. been explored, we suspected that their strained, electron-deficient cyclobutene substituents would make them good electrophiles for conjugate addition reactions (e.g., "thiol-Michael" addition). To test this idea, TCND-(CO2Me)2 was exposed to dodecanethiol (1.0 equiv) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10 mol %) in CDCl3 for 30 min (Table , entry 1). Gratifyingly, 47% conversion was observed under these conditions, while 0% conversion was observed in the absence of DBU. Polar solvents are known to accelerate conjugate addition reactions that involve polar mechanisms; 46 when DMF-d7 was used as the solvent for this reaction, 87% conversion was achieved in 30 min using only 1 mol% DBU (Table , entry 2).