PMID: 11925226Apr 2, 2002Paper

Addition of bromine chloride and iodine monochloride to carbonyl-conjugated, acetylenic ketones: synthesis and mechanisms

The Journal of Organic Chemistry
Victor L HeasleyDale F Shellhamer

Abstract

The reactions of 3-butyn-2-one (1), 3-hexyn-2-one (2), and 4-phenyl-3-butyn-2-one (3) with bromine chloride (BrCl) and iodine monochloride (ICl) in CH(2)Cl(2), CH(2)Cl(2)/pyridine, and MeOH are described. The data show that the major products in CH(2)Cl(2) are (Z)-AM (anti-Markovnikov) regioisomers. With the exception of 3 and ICl, the (E)-AM regioisomers predominate when pyridine was added as an acid scavenger. Minor amounts of the M regioisomers were formed with 1 and 2 and BrCl. The percentage of M regioisomer increased significantly with 1 and BrCl in MeOH, but MeOH had little affect on the other reactions. Isolation and stability of the products are discussed. Detailed evidence for the structures of the products, involving a combination of MS, (1)H and (13)C NMR, and IR, is presented; HRMS analyses are provided as proofs for all of the products. The acid-catalyzed mechanism and the halonium ion mechanism are considered as possible pathways in the formation of the products.

Citations

Sep 28, 2010·Chemical Communications : Chem Comm·Zhengwang ChenChaorong Qi
Jun 24, 2016·Organic & Biomolecular Chemistry·Claudio R DantasPaulo H Menezes
Oct 24, 2019·Chemical Reviews·Carmen NájeraMiguel Yus
Dec 20, 2003·The Journal of Organic Chemistry·Fabio BellinaStephane Viel
Jan 17, 2004·The Journal of Organic Chemistry·Ravi S OruguntyKhalil Abboud

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