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

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

Journal

Open Chemistry
ISSN: 2391-5420

Output data

Year: 2012, Volume: 10, Number: 2, Pages: 360-367 Pages count : 8 DOI: 10.2478/s11532-011-0158-8

Authors

Terent’ev Alexander O. ¹ , Krylov Igor B. ¹ , Vil Vera A. ¹ , Pastukhova Zhanna Yu. ¹ , Fastov Sergey A. ² , Nikishin Gennady I. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation
2	JSC “Nano Technology and Innovations”, 124482, Zelenograd, Russian Federation

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.

Terent’ev A.O. , Krylov I.B. , Vil V.A. , Pastukhova Z.Y. , Fastov S.A. , Nikishin G.I.
Synthesis of dibromo ketones by the reaction of the environmentally benign H2O2-HBr system with oximes
Open Chemistry. 2012. V.10. N2. P.360-367. DOI: 10.2478/s11532-011-0158-8 WOS Scopus OpenAlex

≡ Web of science:	WOS:000299703800011
≡ Scopus:	2-s2.0-84862691992
≡ OpenAlex:	W2012208581