ChemInform Abstract: Addition of Bromine Chloride and Iodine Monochloride to Carbonyl‐Conjugated, Acetylenic Ketones: Synthesis and Mechanisms.

Abstract

Addition of Bromine Chloride and Iodine Monochloride to Carbonyl-Conjugated, Acetylenic Ketones: Synthesis and Mechanisms.-Addition of BrCl and ICl to the acetylenic ketones (I), (IV), and (VII) is studied under different conditions. Generally, in CH 2 Cl 2 (Z)-anti-Markovnikov isomers predominate, whereas in CH 2 Cl 2 /Py (E)-anti-Markovnikov isomers are mainly formed. In MeOH, addition of BrCl to the ketone (I) gives significant amounts of the Markovnikov isomer. Acid-catalyzed mechanism and halonium ion mechanism are considered as possible pathways. -(HEASLEY, VICTOR L.; BUCZALA, DEANNA M.; CHAPPELL, ALFRED E.; HILL, DAVID J.; WHISENAND, JOSH M.; SHELLHAMER, DALE F.; J.