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Kinetics and Mechanism of the Olefin-Forming Elimination Producing Phenylsulfonylethene

M. Sedlák, J. Hanusek, and J. Kaválek

Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, CZ-532 10 Pardubice

 

E-mail: Milos.Sedlak@upce.cz, Jiri.Hanusek@upce.cz, Jaromir.Kavalek@upce.cz

Abstract: [2-(Phenylsulfonyl)ethyl]trimethylammonium iodide, its 2,2-dideuterio derivative, and 1-chloro-2-(phenylsulfonyl)ethane have been synthesized, and the kinetics of their elimination reaction giving phenylsulfonylethene have been studied in methanolic solutions of acetate, triethylamine, morpholine, and butylamine buffers. The kinetic experiments show that the reaction is specific-base-catalyzed and its rate is independent of the ionic strength, and the primary isotope effect is 3.5. The results of kinetic measurements are discussed from the point of view of the E1cB mechanism.

Full paper in Portable Document Format: 543a183.pdf

 

Chemical Papers 54 (3) 183–186 (2000)

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