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Title: Kinetics and mechanism of oxidation of aliphatic alcohols by [bis(trifluoroacetoxy)iodo]benzene
Authors: Banerjia, Jayshree
Sharmaa, Pradeep K
Banerjib, Kalyan K
Issue Date: Aug-2008
Publisher: CSIR
Series/Report no.: Int.Cl.⁸ C07B33/00
Abstract: The oxidation of some aliphatic alcohols by [bis(trifluoro-acetoxy)iodo]benzene (TFAIB) in aqueous acetic acid solution leads to the formation of the corresponding carbonyl compounds. The reaction is first order in TFAIB and a Michaelis-Menten kinetics is obtained with respect to the alcohols. The reaction shows a first order dependence on hydrogen ions. The oxidation of [1,1–²H₂]ethanol and [2-²H]propan-2-ol exhibits the presence of a substantial primary kinetic isotope effect at 298 K (kH/kD = 3.64 and 3.89 respectively). The rate of disproportionation of the intermediate is susceptible to both polar and steric effects of the substituents. A suitable mechanism has also been proposed.
Description: 1213-1217
ISSN: 0376-4710
Appears in Collections:IJC-A Vol.47A(08) [August 2008]

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