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Chloro(bromo)vinyl ketones and 2,2-Dichloroacrolein in Reactions with Hydrazines

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Abstract

Reactions of 2,2-dichlorovinyl and 2,2-dibromovinyl ketones with alkylhydrazines afford respectively 1-R-3-alkyl(aryl)-5-chloro- or 5-bromopyrazoles in preparative yields. The dichloroacrolein forms with alkylhydrazines and dimethylhydrazine only the corresponding hydrazones. Quantum-chemical calculations were performed characterizing the structure of the obtained ketones and dichloroacrolein alkylhydrazones, of dichloroacrolein dimethylhydrazone, of 1-alkyl-5-chloropyrazolinium halides, and 1-alkyl-5-chloropyrazoles.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    G. V. Bozhenkov, G. G. Levkovskaya, A. N. Mirskova, G. V. Dolgushin, L. I. Larina & P. E. Ushakov

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  1. G. V. Bozhenkov
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  2. G. G. Levkovskaya
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  3. A. N. Mirskova
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  4. G. V. Dolgushin
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  5. L. I. Larina
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  6. P. E. Ushakov
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Bozhenkov, G.V., Levkovskaya, G.G., Mirskova, A.N. et al. Chloro(bromo)vinyl ketones and 2,2-Dichloroacrolein in Reactions with Hydrazines. Russian Journal of Organic Chemistry 39, 1069–1075 (2003). https://doi.org/10.1023/B:RUJO.0000010172.72180.4f

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  • DOI: https://doi.org/10.1023/B:RUJO.0000010172.72180.4f

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