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

• Authors: Alexander Terent’ev , Igor Krylov , Vera Vil’ , Zhanna Pastukhova , Sergey Fastov , Gennady Nikishin
• Languages of publication: EN

Abstracts

EN

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

EN

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

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 2
• Pages: 360-367

Dates

published

1 - 4 - 2012

online

29 - 1 - 2012

Contributors

author

Alexander Terent’ev

• N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation

author

Igor Krylov

• N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation

author

Vera Vil’

• N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation

author

Zhanna Pastukhova

• N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation

author

Sergey Fastov

• JSC “Nano Technology and Innovations”, 124482, Zelenograd, Russian Federation

author

Gennady Nikishin

• N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation

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Identifiers

DOI

10.2478/s11532-011-0158-8