Dichlorination of Alkenes Using 1, 3‐Dichloro‐5, 5‐Dimethylhydantoin and ZnCl2. Issue 39 (21st October 2019)

• Record Type: Journal Article
• Authors: Ángel, Alix Y. Bastidas; Bragança, Emanuella F.; Alberto, Eduardo E.
• Is Part Of: ChemistrySelect. Volume 4:Issue 39(2019)
• Page Start: 11548
• Page End: 11552
• Publication Date: 2019-10-21
• Subjects: Dichlorination of Alkenes -- 1, 3-Dichloro-5, 5-Dimethylhydantoin/ZnCl2 -- Halogenation -- Safe Chlorine Gas Surrogate; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201902568
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Electron‐deficient and electron‐rich alkenes can be efficiently converted to vicinal dichlorides employing a mixture of 1, 3‐dichloro‐5, 5‐dimethylhydantoin (DCDMH) and zinc chloride. This straightforward protocol offers an easier to handle and safer alternative to the use of chlorine gas or other common chlorinating agents. Experimental evidences suggest that the solubility of the chloride salt is essential for the formation of a chlorine/trichloride anion as the effective chlorinating agent. Abstract : The mixture of 1, 3‐dichloro‐5, 5‐dimethylhydantoin (DCDMH) and zinc chloride represents an inexpensive, easy to handle and safe reagent combination for the ionic dichlorination of electron‐rich and electron‐poor alkenes. The solubility of the chloride source is key for the reaction outcome. The chloride ion promotes the activation of DCDMH producing the halogenating species chlorine / trichoride anion in situ .