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Kinetics and mechanism of oxidation of alcohols

Kinetics and mechanism of oxidation of alcohols Monatsh Chem (2013) 144:307–312 DOI 10.1007/s00706-012-0826-1 OR IGINAL PAPER Abdulhameed Laila Received: 9 March 2012 / Accepted: 10 July 2012 / Published online: 4 August 2012 Springer-Verlag 2012 Abstract This paper describes the kinetics and mecha- Bis(quinuclidine)bromine(I) bromide (BQB), a two- nism of oxidation of several monohydric alcohols to the coordinate halogen(I) species containing a central hyper- corresponding aldehydes and ketones by bis(quinucli- valent bromine, has been reported as an efficient oxidizing dine)bromine(I) bromide in the presence of pyridinium reagent for alcohols [13], but the mechanistic pathway has trifluoroacetate. All evidence from the thermodynamic never been deeply investigated. We therefore aimed to parameters, deuterium kinetic isotope effect, and Hammett study the kinetics of the oxidation of primary and sec- reaction constants supports a two-step mechanism and ondary alcohols with the oxidant BQB in the presence of suggests that the transfer of hydride ion from the substrate pyridinium trifluoroacetate. to the oxidant is the rate-determining step. One approach to elucidate the oxidation mechanism is through the use of structure–reactivity profiles coupled Keywords Carbonyl compounds  Isotope effects  with isotope effect measurements. Therefore, the rates of Structure–reactivity relationship  Rate constants oxidation of meta- and para-substituted benzyl alcohol have been http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

Kinetics and mechanism of oxidation of alcohols

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References (21)

Publisher
Springer Journals
Copyright
Copyright © 2012 by Springer-Verlag
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
DOI
10.1007/s00706-012-0826-1
Publisher site
See Article on Publisher Site

Abstract

Monatsh Chem (2013) 144:307–312 DOI 10.1007/s00706-012-0826-1 OR IGINAL PAPER Abdulhameed Laila Received: 9 March 2012 / Accepted: 10 July 2012 / Published online: 4 August 2012 Springer-Verlag 2012 Abstract This paper describes the kinetics and mecha- Bis(quinuclidine)bromine(I) bromide (BQB), a two- nism of oxidation of several monohydric alcohols to the coordinate halogen(I) species containing a central hyper- corresponding aldehydes and ketones by bis(quinucli- valent bromine, has been reported as an efficient oxidizing dine)bromine(I) bromide in the presence of pyridinium reagent for alcohols [13], but the mechanistic pathway has trifluoroacetate. All evidence from the thermodynamic never been deeply investigated. We therefore aimed to parameters, deuterium kinetic isotope effect, and Hammett study the kinetics of the oxidation of primary and sec- reaction constants supports a two-step mechanism and ondary alcohols with the oxidant BQB in the presence of suggests that the transfer of hydride ion from the substrate pyridinium trifluoroacetate. to the oxidant is the rate-determining step. One approach to elucidate the oxidation mechanism is through the use of structure–reactivity profiles coupled Keywords Carbonyl compounds  Isotope effects  with isotope effect measurements. Therefore, the rates of Structure–reactivity relationship  Rate constants oxidation of meta- and para-substituted benzyl alcohol have been

Journal

Monatshefte für Chemie - Chemical Monthly – Springer Journals

Published: Aug 4, 2012

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