Journal of the American Chemical Society, Vol.125, No.24, 7307-7312, 2003
Mechanism of electrophilic chlorination: Experimental determination of a geometrical requirement for chlorine transfer by the endocyclic restriction test
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.