ChemInform Abstract: Primary Vinyl Cations in Solution: Kinetics and Products of β,β-Disubstituted Alkenyl(aryl)iodonium Triflate Fragmentations.

✍ Scribed by Robert J. Hinkle; Anne J. McNeil; Quinn A. Thomas; Marie N. Andrews

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199951084

✦ Synopsis

The title iodonium triflates (I) and (II) are decomposed in CHCl 3 at 20-35 • C to give a stereoisomeric mixture of six enol triflates, as result of heterolytic C-I bond cleavage followed by direct TfO -trapping of the generated primary vinyl cation (III). Incorporation of strongly electron-withdrawing trifluoromethyl groups into the phenyl ring allows the determination of kinetic parameters for the decompositions as well as a quantitative evaluation of the effects of the electron-withdrawing groups on the reaction. -(HINKLE,