Computational model of the formation of novel nitronorbornene analogs via Diels–Alder process

In this study, we employed Density Functional Theory (DFT) to analyze the Diels–Alder reaction between isomeric methylcyclopentadienes and (2E)-3-phenyl-2-nitroprop-2-enenitrile. Our computational approach focused on evaluating thermodynamic and kinetic parameters to elucidate the reaction mechanisms. The findings indicate that pathways leading to products with an endo-oriented nitro group proceed via a two-step mechanism involving a heterocyclic intermediate. Conversely, exo-oriented nitro group products are formed through a one-step, albeit asynchronous, mechanism. These insights contribute to a deeper understanding of the mechanistic pathways in Diels–Alder reactions, offering valuable information for optimizing industrial processes and designing novel synthetic routes.