Computational study of organized cycloaddition reactions with pyrrole moiety as a diene

Abstract

Computational studies were performed to determine the reactivity of pyrrole as the diene in cycloaddition reactions, and to investigate the necessary chemical transformations that would make pyrrole an effective diene. Also, it was of interest to establish what chemical transformations would lead exclusively to an exo or to endo cycloadducts. The study was performed by using the pyrrole ring bond order uniformity, transition state six-membered ring bond order uniformity, frontier molecular orbital energy changes (inertia principle), and activation energies. Synthetic routes for the preparation of one isomer over another were proposed.