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Kinetics and mechanism of the oxidation of diols by pyridinium bromochromate

โœ Scribed by P. Surya Chandra Rao; Deepa Suri; Seema Kothari; Kalyan K. Banerji

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
122 KB
Volume
30
Category
Article
ISSN
0538-8066

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โœฆ Synopsis

The kinetics of oxidation of four vicinal diols, four nonvicinal diols, and one of their monoethers by pyridinium bromochromate (PBC) have been studied in dimethyl sulfoxide. The main product of oxidation is the corresponding hydroxyaldehyde. The reaction is first-order with respect to each the diol and PBC. The reaction is acid-catalyzed and the acid dependence has the form:

The

obs a primary kinetic isotope effect ( at ). The reaction has been studied in 19 k /k ฯญ 6.70 298 K H D organic solvents including dimethyl sulfoxide and the solvent effect has been analyzed using 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.

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