Kinetics and mechanism of the oxidation of aliphatic primary alcohols by imidazolium fluorochromate
The oxidation of nine aliphatic primary alcohols by imidazolium fluorochromate (IFC) in dimethylsulphoxide leads to the formation of corresponding aldehydes. The reaction is first order with respect to IFC. A Michaelis-Menten type kinetics is observed with respect to alcohols. The reaction is promoted by hydrogen ions; the hydrogen-ion dependence has the form : kobs = a + b [H+]. The oxidation of [1,1- 2H2]ethanol (MeCD2OH) exhibits a substantial primary kinetic isotope effect (kH/kD = 5.87 at 298 K). The reaction has been studied in nineteen different organic solvents. The solvent effect was analysed using Taft's and Swain's multiparametric equations. The rate of oxidation is susceptible to both polar and steric effects of the substituents. A suitable mechanism has been proposed.
Gehlot,Gilla,Mishra,Sharma, Vinita
experimental part
p. 685 - 692
(2012/04/04)
Oxidation of some vicinal and non-vicinal diols by morpholinium chlorochromate: A kinetic and mechanistic study
The kinetics of oxidation of four vicinal, four non-vicinal diols and two of their monoethers by morpholinium chlorochromate (MCC) have been studied in dimethylsulphoxide (DMSO). The main product of oxidation is the corresponding hydroxycarbonyl compound. The reaction is first order in MCC and the diols. The reaction is catalysed by hydrogen ions. The hydrogen ion dependence is taking the form : kobs = a + b [H+]. The oxidation of [1,1,2,2-2H4]ethanediol exhibits a substantial primary kinetic isotope effect (kH/kD = 5.82 at 298 K). The reaction has been studied in nineteen different organic solvents and the solvent effect has been analysed using Taft's and Swain's multiparametric equations. The temperature dependence of the kinetic isotope effect indicates the presence of a symmetrical transition state in the rate-determining step. A suitable mechanism has been proposed.
Barthora,Baghmar,Agarwal,Sharma, Vinita
experimental part
p. 677 - 683
(2012/04/10)
Oxidation of aliphatic primary alcohols by morpholinium chlorochromate: A kinetic and mechanistic approach
The oxidation of nine aliphatic primary alcohols by morpholinium chlorochromate (MCC) in dimethylsulfoxide leads to the transformation of alcohols to the corresponding aldehydes. The reaction is first order with respect to both MCC and the alcohol both. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form: kobs = a + A[H +]. The oxidation of [1,1-2H2]ethanol (MeCD2OH) exhibits a substantial primary kinetic isotope effect. The reaction has been studied in nineteen different organic solvents. The solvent effect was analysed using Taft's and Swain's multiparametric equations. The rate of oxidation is susceptible to both polar and steric effects of the substituents. A suitable mechanism has been proposed.
Choudhary,Yajurvedi,Soni,Agarwa,Sharma, Vinita
experimental part
p. 1061 - 1066
(2011/05/05)
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