Kinetic investigations of the electrochemical bromination of peracetylated d-glucal in organic solvents

[Display omitted] ► Electrochemical oxidation of a bromide salt into tribromide and bromine species. ► Reactivity of tribromide and bromine species towards 3,4,6-tri-O-acetyl-d-glucal. ► Kinetic investigations as a function of the nature of both the solvent and the brominated species. Cyclic voltamm...

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Bibliographic Details
Published in:Electrochimica acta 2011-11, Vol.56 (27), p.9968-9972
Main Authors: Šegan, Dejan, Vukićević, Rastko D., Šegan, Sandra, Sojic, Neso, Buriez, Olivier, Manojlović, Dragan
Format: Article
Language:English
Subjects:
Acetonitrile
Bromides
Bromination
Chemistry
Competition
Cyclic voltammetry
Dichloromethane
Electrochemistry
Exact sciences and technology
General and physical chemistry
Glycal
Kinetic
Kinetics and mechanism of reactions
Polarity
Solvents
Voltammetry
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Summary:[Display omitted] ► Electrochemical oxidation of a bromide salt into tribromide and bromine species. ► Reactivity of tribromide and bromine species towards 3,4,6-tri-O-acetyl-d-glucal. ► Kinetic investigations as a function of the nature of both the solvent and the brominated species. Cyclic voltammetry and ultramicroelectrodes were used to investigate the kinetic aspects of the electrochemical bromination of 3,4,6-tri-O-acetyl-d-glucal (1) in acetonitrile (AN), dichloromethane (DCM), and dimethylsulfoxide (DMSO). Qualitative and quantitative results, determined notably from the kinetic parameter [glucal]/v representing the competition between glucal concentration and time, clearly showed that glucal bromination depended on the nature of both the solvent and the in situ electrogenerated reactive brominated species (Br2 or Br3−) obtained from the oxidation of a bromide salt. It was especially shown that Br2 reacted more rapidly than Br3− towards (1). On the other hand, the reactivity of both brominated species appeared to follow the solvent polarity order since the highest reactivity was obtained in DMSO whereas the lowest one was found in DCM.
ISSN:0013-4686
1873-3859
DOI:10.1016/j.electacta.2011.08.085