Issue 8, 1988

Kinetics and mechanism of reactions between 2-phenylethyl benzenesulphonates and anilines in methanol

Abstract

Kinetics of reactions between 2-phenylethyl benzenesulphonates and anilines in methanol at 65.0 °C have been studied; the mechanism is discussed on the basis of cross interaction constants, ρij. The overall reaction was found to proceed by a dissociative SN2 mechanism with a relatively small degree of aryl participation. The fraction of the phenonium ion intermediate captured by the nucleophile, aniline, in the aryl-assisted pathway has been shown to increase with a stronger nucleophile, and a four-centre transition state in an intermolecular SNi mechanism is suggested for the aryl-unassisted pathway.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1988, 1537-1540

Kinetics and mechanism of reactions between 2-phenylethyl benzenesulphonates and anilines in methanol

I. Lee, Y. H. Choi, H. W. Lee and B. C. Lee, J. Chem. Soc., Perkin Trans. 2, 1988, 1537 DOI: 10.1039/P29880001537

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