ChemInform Abstract: The Activation of Carbon—Chlorine Bonds in Per- and Polyfluoroalkyl Chlorides: DMSO-Induced Hydroperfluoroalkylation of Alkenes and Alkynes with Sodium Dithionite.

✍ Scribed by Zheng-Yu Long; Qing-Yun Chen

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 44 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199945083

✦ Synopsis

The Activation of Carbon-Chlorine Bonds in Per-and Polyfluoroalkyl Chlorides: DMSO-Induced Hydroperfluoroalkylation of Alkenes and Alkynes with Sodium Dithionite.

-In DMSO, addition reactions of perfluoroalkyl chlorides to alkenes or alkynes occur smoothly in the presence of Na 2 S 2 O 4 and NaHCO 3 to give the corresponding adducts of type (III), (V), (VII), (XI), or (XII). Treatment of ω-chloro or ω-iodo perfluoroalkyl chlorides with ¿3 equivalents of alkenes affords symmetrically disubstituted alkanes like (IX). In addition, in the absence of alkenes or alkynes the fluoroalkyl chlorides can be converted to their sulfinate salts and sulfonyl chlorides. -(LONG,