In this study, ReaxFF molecular dynamics simulations were benchmarked and used to study the relative kinetics of the retro Diels-Alder reaction between furan and N-methylmaleimide. This reaction is very important for the creation of polymer networks with self-healing and recyclable properties, since they can be used as reversible linkers in the network. So far, the reversible Diels-Alder reaction has not yet been studied by using reactive molecular dynamics simulations. This work is, thus, the first step in simulating a covalent adaptable network (CAN) using Diels-Alder reactions as reversible linkers. For both endo and exo, the bond breaking in 40 product molecules was simulated using the bond boost method and the endo/exo ratio was evaluated. This ratio was benchmarked against density functional theory (DFT) and experimental results for a changing set of bond boost parameters. Given their importance to understand how the CAN performs, the effect of the addition of a polymer backbone and the effect of temperature were successfully simulated using our newly parametrized reactive force field.