Mechanistic studies of the oxidation of substituted phenethyl alcohols by N-metallo-N-haloarylsulphonamides: kinetic isotope studies

Rangappa, K. S. (2001) Mechanistic studies of the oxidation of substituted phenethyl alcohols by N-metallo-N-haloarylsulphonamides: kinetic isotope studies. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 14 (10). pp. 684-690.

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Official URL: http://dx.doi.org/10.1002/poc.415

Abstract

The oxidation of para-substituted phenethyl alcohols (PEA, 2) by N-metallo-N-haloarylsulphonamides (1) in the presence of dilate HCl to the corresponding phenacetaldehydes (4) is first order with respect to oxidant (1) and H+] and a fractional order each in PEA] and Cl-]. Addition of the reaction product (3), ionic strength variations and variation of dielectric constant of the medium had no effect on the rate. The oxidation of PhCH2CD2OH (2) exhibited a substantial primary kinetic isotope effect (k(H)/k(D) = 5.83). The rates correlate satisfactorily with the Hammett free energy relationship. The activation parameters AH(#), AS(#), AG(#) and logA were calculated for the reaction. The proposed mechanism is consistent with the observed results. Copyright (C) 2001 John Wiley & Sons, Ltd.

Item Type: Article
Uncontrolled Keywords: substituted phenethyl alcohols; oxidation; N-metallo-N-haloarylsulphonamides; mechanism; kinetic isotope effect
Subjects: Physical Sciences > Chemistry
Divisions: PG Campuses > Manasagangotri, Mysore > Chemistry
Depositing User: Users 12 not found.
Date Deposited: 19 Apr 2013 13:40
Last Modified: 15 May 2013 06:47
URI: http://eprints.uni-mysore.ac.in/id/eprint/4744

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