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Transformations of conjugated enamines of the imidazolidine 1-oxide series in the Vilsmeier-Haack reaction Full article

Journal Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171
Output data Year: 2007, Volume: 56, Number: 6, Pages: 1210-1215 Pages count : 6 DOI: 10.1007/s11172-007-0183-0
Tags nitroxides; enaminones; nitroenamine; Vilsmeier-Haack reaction; imidazolidines
Authors Becker Ch.S. 1 , Roshchupkina G.I. 2 , Rybalova T.V. 2 , Gatilov Yu.V. 2 , Reznikov V.A. 2
Affiliations
1 Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation
2 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

Abstract: In some cases, the reactions of enaminones of the imidazolidine 1-oxide series with the Vilsmeier reagent afford electrophilic substitution products containing the dimethyl-aminomethylene group. In an acidic medium, these products undergo either hydrolytic elimination of the dimethylaminomethylene moiety or hydrolysis of the latter to form the aldehyde group. The reaction of nitroenamine, which is a derivative of imidazolidine 1-oxide, with the Vilsmeier reagent produces furoxane, viz., the nitroxyl biradical. Reduction of the latter affords the dioxime biradical.
Cite: Becker C.S. , Roshchupkina G.I. , Rybalova T.V. , Gatilov Y.V. , Reznikov V.A.
Transformations of conjugated enamines of the imidazolidine 1-oxide series in the Vilsmeier-Haack reaction
Russian Chemical Bulletin. 2007. V.56. N6. P.1210-1215. DOI: 10.1007/s11172-007-0183-0 WOS Scopus РИНЦ OpenAlex
Original: Мельникова-Беккер К.С. , Рощупкина Г.И. , Рыбалова Т.В. , Гатилов Ю.В. , Резников В.А.
Превращения сопряженных енаминов ряда имидазолидин-1-оксила в реакции Вильсмайера-Хаака
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2007. №6. С.1165-1170.. РИНЦ
Dates:
Published print: Jun 1, 2007
Identifiers:
Web of science: WOS:000251971700018
Scopus: 2-s2.0-36949002086
Elibrary: 13549843
OpenAlex: W2951240354
Citing:
DB Citing
Web of science 1
Scopus 1
Elibrary 1
OpenAlex 1
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