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|Title:||Kinetics and mechanism of oxidation of some α-hydoxy acids by butyltriphenylphosphonium dichromate|
Banerji, Kalyan K
|Abstract:||The oxidation of lactic acid, mandelic acid and nine monosubstituted mandelic acids by butyltriphenylphosphonium dichromate (BTPPD) in dimethylsulphoxide (DMSO) leads to the formation of the corresponding oxoacids. The reaction is first order in BTPPD. The order in the reductant and hydrogen ions is two. The oxidation of α-deuteriomandelic acid exhibited the presence of a substantial kinetic isotope effect. The reaction has been studied in nineteen organic solvents and the solvent effect analyzed using multiparametric equations. It is found that the cation-solvating power plays the major role. The rate of oxidation of substituted mandelic acids shows an excellent correlation with the Hammett σ values. The reaction constants are negative. Suitable mechanism has been proposed.|
|Appears in Collections:||IJC-A Vol.39A(07) [July 2000]|
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