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Title: Kinetics and mechanism of oxidation of some diols by benzyltrimethylammonium chlorobromate
Authors: Bhatt, Monica
Sharma, Pradeep K
Banerji, Kalyan K
Issue Date: Apr-2002
Publisher: NISCAIR-CSIR, India
Abstract: Kinetics of oxidation of five vicinal, four non-vicinal diols, and one of their monoethers by benzyltrimethylammonium chlorobromate (BTMACB) have been studied. The vicinal diols yield the products arising out of the glycol-bond fission while the other diols afford the hydroxycarbonyl compounds. The reaction is first order with respect to diols and the BTMACB. The reaction failed to induce the polymerization of acrylonitrile. There is no effect of benzyltrimethylammonium chloride or potassium bromide on the reaction rate. The proposed reactive oxidizing species is chlorobromate ion. The effect of solvent composition indicated that the rate increases with an increase in the polarity of the solvent. The oxidation of [1,1,2,2-2H4]ethanediol show an absence of primary kinetic isotope effect. The value of solvent isotope effect, k(H2O)/k(D2O), at 288 K for the oxidation of ethanediol, propane-1,3-diol and 3-methoxybutan-1-ol are 3.32, 1.04 and 1.01 respectively. A cyclic mechanism involving a glycol-bond fission has been proposed for the oxidation of the vicinal diols. The other diols are oxidised by a hydride-transfer mechanism, as are monohydric alcohols.
Page(s): 826-831
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.41B(04) [April 2002]

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