Kinetic investigations of the electrochemical bromination of peracetylated D-glucal in organic solvents
Authorized Users Only
2011
Authors
Šegan, Dejan
Vukicevic, Rastko D.
Šegan, Sandra

Šojić, Nešo

Buriez, Olivier
Manojlović, Dragan

Article (Published version)

Metadata
Show full item recordAbstract
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]/nu 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 (Br-2 or Br-3(-)) obtained from the oxidation of a bromide salt. It was especially shown that Br-2 reacted more rapidly than Br-3(-) 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.
Keywords:
Kinetic / Bromination / Glycal / Cyclic voltammetrySource:
Electrochimica Acta, 2011, 56, 27, 9968-9972Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Projects:
- Ministry of Science of the Republic of Serbia
DOI: 10.1016/j.electacta.2011.08.085
ISSN: 0013-4686