These monomers were enumerated based on known synthetic precursors (alkenes, alkynes, allenes, and benzynes) and common substituents (Figure ). To screen for thermodynamic monomer stabilityindependent of the kineticsthe rDA reaction free energies were calculated at 200 °C (see SI for more details). To screen for the FROMP driving force, the ring strain of a monomer, which generates the heat necessary to propagate the front upon ring opening, we quantified the ring strain through the calculated enthalpy of a homodesmotic reaction of the monomer with ethene at 200 o C. As shown in Figure , the furan-alkenes, as well as the majority of the furan-allenes and furan-alkynes, exhibit negative rDA free energies, suggesting the rDA reaction is thermodynamically preferred for these monomers and they are not stable at the front. In contrast, all the furan-benzynes (Table ) display high free energies of rDA (>40 kcal/mol) and high ring strains (>20 kcal/mol), rendering them a particularly promising class of monomers for FROMP. No oxa-benzonorbornadienes are predicted to undergo rDA at this temperature, having an equilibrium constant on the order of 10 -19 (as a comparison, only 2% of endo-DCPD product is present at its equilibrium concentration at 200 °C). This suggests that rDA should likely be a minimal source of competition to polymerization of oxa-benzonorbornadienes, across a range of chemistries with potentially differing ring-opening kinetics. Moreover, the diverse chemistries present within the furan-benzyne family all display desirable energetics, suggesting that chemical modifications to both diene and dienophile can be used strategically to tune FROMP kinetics and resulting mechanical properties without compromising monomer stability (Figure , Table ). As such, the family of furan-benzyne monomers are positioned to be promising, contingent on kinetic considerations, and were selected for experimental exploration and characterization.