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Synthesis, structure, and characteristics of 1,2-dichlorovinyl alkyl ketones

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Abstract

A method of alkyl 1,2-dichlorovinyl ketones preparation from acyl halides and 1,2-dichloroethylene was developed. The configurational equilibrium and electronic structure of alkyl 1,2-dichlorovinyl ketones was investigated by IR, 1H and 13C NMR spectroscopy, by measuring dipole moments, and by quantum-chemical calculations using methods RHF and B3LYP in the basis 6–311++G (d,p). Alkyl 1,2-dichlorovinyl ketones are stable in the Z, s-cis-configuration where the olefin proton is involved into an intramolecular hydrogen bond with the oxygen of the carbonyl group. Reaction of 1,2-dichlorovinyl ketones with alkylhydrazines afforded 1-alkyl-3-alkyl-4-chloropyrazoles. The reaction of alkyl 1,2-dichlorovinyl ketones with 1,1-dimethylhydrazine involved dehydrochlorination and afforded 1,1-dimethylhydrazinium hydrochloride and a mixture of compounds with uncertain structure.

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Authors and Affiliations

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

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

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  1. G. V. Bozhenkov
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  2. G. G. Leckovskaya
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  3. L. I. Larina
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  4. P. E. Ushakov
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  5. G. V. Dolgushin
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  6. A. N. Mirskova
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Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 11, 2004, pp. 1632–1640.

Original Russian Text Copyright © 2004 by Bozhenkov, Leckovskaya, Larina, Ushakov, Dolgushin, Mirskova.

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Bozhenkov, G.V., Leckovskaya, G.G., Larina, L.I. et al. Synthesis, structure, and characteristics of 1,2-dichlorovinyl alkyl ketones. Russ J Org Chem 40, 1583–1592 (2004). https://doi.org/10.1007/s11178-005-0064-7

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  • DOI: https://doi.org/10.1007/s11178-005-0064-7

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