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Open Chemistry

formerly Central European Journal of Chemistry

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Volume 10, Issue 2

Issues

Volume 13 (2015)

Synthesis of dibromo ketones by the reaction of the environmentally benign H2O2-HBr system with oximes

Alexander Terent’ev / Igor Krylov / Vera Vil’ / Zhanna Pastukhova / Sergey Fastov / Gennady Nikishin
Published Online: 2012-01-29 | DOI: https://doi.org/10.2478/s11532-011-0158-8

Abstract

It was found that oximes undergo deoximation in the presence of the H2O2aq-HBraq system to form ketones and bromo ketones. This reaction provided the basis for the synthesis of dibromo ketones in yields varying from 40% to 94%. This method is environmentally friendly, sustainable, and easy to perform. The results of this investigation extend the potential of the use of oximes for the protection of carbonyl group, thus offering the ability to perform not only conventional deoximation but also the subsequent bromination of ketones. The reaction is easily scaled up and dibromo ketones can be prepared in gram amounts.

Keywords: Oximes; Dibromo ketones; Bromination; Hydrogen peroxide; Hydrobromic acid

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About the article

Published Online: 2012-01-29

Published in Print: 2012-04-01


Citation Information: Open Chemistry, Volume 10, Issue 2, Pages 360–367, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-011-0158-8.

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© 2012 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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