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ISSUE 6

Year 2007, Month 6 (Section Full Articles, Page 1210)

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

Ch. S. Becker, G. I. Roshchupkina, T. V. Rybalova, Yu. V. Gatilov, and V. A. Reznikov

In some cases, the reactions of enaminones of the imidazolidine 1-oxide series with the Vilsmeier reagent afford electrophilic substitution products containing the dimethylaminomethylene 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 1oxide, with the Vilsmeier reagent produces furoxane, viz., the nitroxyl biradical. Reduction of the latter affords the dioxime biradical.

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