Mechanism of Electrophilic Chlorination: Experimental Determination of a Geometrical Requirement for Chlorine Transfer by the Endocyclic Restriction Test

Abstract

An endocyclic restriction test for acid-catalyzed transfer of chlorine from a protonated chloroamine to an aromatic ring provides data that are consistent with a transition structure with a large bond angle between the entering and leaving groups around chlorine. These results rule out a dissociative mechanism or a mechanism that has an oblique angle between the entering and leaving groups.