Kinetics and mechanism of oxidation of primary alcohols by pyridinium hydrobromide perbromide
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 205-208
- https://doi.org/10.1039/p29930000205
Abstract
Oxidation of nine primary aliphatic alcohols by pyridinium hydrobromide perbromide (PHPB) in aqueous acetic acid leads to the formation of the corresponding aldehydes. The reaction is first order with respect to PHPB. Michaelis-Menten-type kinetics are observed with respect to the alcohol. The oxidation of [1,1-2H2]ethanol (MeCD2OH) exhibits a substantial kinetic isotopic effect. The effect of solvent composition indicates that the transition state is more polar than the reactants. The reaction is susceptible to both polar and steric effects of the substituents. A mechanism involving transfer of a hydride ion from the alcohol to the oxidant has been proposed.Keywords
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