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Direct C-nitration of cyclic alpha,beta-unsaturated oximes under the action of sodium nitrite and acetic acid in methanol Full article

Journal Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171
Output data Year: 2001, Volume: 50, Number: 8, Pages: 1410-1418 Pages count : 9 DOI: 10.1023/A:1012785007135
Tags alpha,beta-unsaturated oximes; conjugated ketones; nitrosation; C-nitration; deoximation; nitroalkenes; circular dichroism
Authors Chibiryaev A.M. 1 , Denisov A.Yu. 2 , Pyshnyi D.V. 1 , Tkachev A.V. 3
Affiliations
1 (Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia
2 Institute of Bioorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 8 prosp. Akad. Lavrent"eva, 630090, Novosibirsk, Russian Federation
3 N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent"eva, 630090, Novosibirsk, Russian Federation

Abstract: Using a number of cyclic alpha,beta-unsaturated oximes of the terpene series and sonic Simplest model compounds as examples, unsaturated oximes bearing a hydrogen atom it the beta-carbon atom were demonstrated to be converted into beta-hydroxyiminonitroalkenes under the action of sodium nitrite and acetic acid in methanol. In the case of the introduction of an alkyl substituent at the terminal carbon atom of the diene C=C-C=NOH fragment, the reaction performed under the same conditions gave rise exclusively to conjugated ketone (a deoximation product).
Cite: Chibiryaev A.M. , Denisov A.Y. , Pyshnyi D.V. , Tkachev A.V.
Direct C-nitration of cyclic alpha,beta-unsaturated oximes under the action of sodium nitrite and acetic acid in methanol
Russian Chemical Bulletin. 2001. V.50. N8. P.1410-1418. DOI: 10.1023/A:1012785007135 WOS Scopus РИНЦ OpenAlex
Identifiers:
Web of science: WOS:000173525900009
Scopus: 2-s2.0-0035528012
Elibrary: 13363793
OpenAlex: W2951922788
Citing:
DB Citing
Web of science 5
Scopus 5
Elibrary 6
OpenAlex 5
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