Origin of the Reactivity Differences of Substituted Aziridines:CN vs CC Bond Breakages

摘要

Aziridines are broadly used as starting materials for various chemical syntheses, and the underlyingreactions (CN vs CC bond breaking accompanied by an attack of a nucleophile or a dipolarophile) arestrongly influenced by the substitution pattern. The present study investigates reaction courses of possiblering-opening reactions accompanied by the attack of a nucleophile for different substitution patterns of theaziridine. Information is obtained through the computation of the underlying potential energy surfacesand reaction paths. The results provide insight into the mechanisms of different ring-opening reactions andexplain how the kinetics and thermodynamics of the reaction are influenced by substituents. This allowspredicting substitution patterns that steer the reaction course to either CN or CC bond cleavage