In situ generation of bromine for micelle-assisted bromination and oxidation -- Restricted access to full text
English, Douglas S.
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Archana Mishra, Zifan Wang and Douglas S. English. (2012). In Situ Generation of Bromine for Micelle-assisted Bromination and Oxidation. -- In Proceedings: 8th Annual Symposium: Graduate Research and Scholarly Projects. Wichita, KS: Wichita State University, p.100-101
This paper describes our recent work in which CTAB (cetyltrimethylammonium bromide) micelles are used as catalytic platforms for performing bromination and oxidation reactions in water. The bromide counter ion is used to prepare Br2 in situ which is subsequently employed as a brominating and oxidizing agent. In this process the bromide is rapidly oxidized to bromine using BPO (benzoic peroxyanhydride). The reaction is facilitated by the micelle which improves the BPO solubility and its proximity with Br-. Several example reactions are discussed including micelle-assisted bromination of cholesterol and methyl styrene along with an example of mild oxidation of benzyl alcohol to form benzaldehyde. These examples illustrate the use of bromine as a mild oxidizing agent and also as a brominating agent. Kinetic studies of Br2 formation and cholesterol bromination are also presented.
Paper presented to the 8th Annual Symposium on Graduate Research and Scholarly Projects (GRASP) held at the Marcus Welcome Center, Wichita State University, April 18, 2012.
Research completed at the Department of Chemistry, Fairmount College of Liberal Arts and Sciences