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.
Lee
Suk Joong
SJ
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Terrazas
Michael S
MS
Pippel
Daniel J
DJ
Beak
Peter
P
D002700:Chloramines / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D002722:Chlorobenzenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D002700:Chloramines; D002722:Chlorobenzenes; D002713:Chlorine