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Title: Kinetics and mechanism of the oxidation of some ⍺-hydroxy carboxylic acids by [bis(trifluoroacetoxy)iodo]benzene
Authors: Banerji, Jayshree
Sharma, Pradeep K
Banerji, Kalyan K
Issue Date: Mar-2007
Publisher: CSIR
IPC Code: Int. Cl. ⁸ C07B33/00
Abstract: The oxidation of ⍺-hydroxy carboxylic acids by [bis(trifluoroacetoxy)iodo]benzene (TFAIB), to the corresponding oxoacids is first order with respect to each, the hydroxy acid, TFAIB and hydrogen ions. The oxidation of ⍺-deuteriomandelic acid (PhCDOHCO₂H) exhibits the presence of a substantial pri-mary isotope effect confirming the cleavage of the ⍺ – C – H bond in the rate-determining step. The rate of oxidation of substi-tuted mandelic acids correlates well with Brown’s ⍺⁺ values with large negative reaction constants. A mechanism involving transfer of a hydride ion from the hydroxy acid to the oxidant has been postulated.
Page(s): 445-448
ISSN: 0376-4710
Appears in Collections:IJC-A Vol.46A(03) [March 2007]

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