Unusual reaction of chloroacetyl chloride with 1,2-dichloroethene. Synthesis and properties of 2-chlorovinyl dichloromethyl ketone

Bozhenkov, G. V.; Savosik, V. A.; Rudyakova, E. V.; Khan, Kha Kuok; Albanov, A. I.; Клыба, Л. В.; Мирскова, А. Н.; Levkovskaya, G. G.

doi:10.1134/s1070428008120038

Cited by 7 publications

(4 citation statements)

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“…1-Bromoethyl 2chlorovinyl ketone (Id) was obtained with admixture of ketone Ie by the reaction of 2-bromopropionyl chloride with 1,1-dichloroethylene catalyzed with aluminum chloride [29]. Dichloroalkyl 2-chlorovinyl ketones If and Ig were prepared by reacting 1chloropropionic acid and chloroacetyl chloride with 1,2-dichloroethylene respectively [42,43]. Physicochemical constants of ketones Iа-If were consistent with the published data.…”

Section: (5)-ethyl- Propyl- and Butylpyrazolessupporting

confidence: 67%

Ratio of 1,3- and 1,5-dialkyl-substituted pyrazoles obtained from chlorovinyl alkyl ketones and alkylhydrazines, 3(5)-pyrazoles and alkyl bromides

et al. 2014

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Unsymmetrically substituted 1,3-and 1,5-dialkylpyrazoles and 1,3-dialkyl-5-chloropyrazoles were prepared. 2-Chlorovinyl ketones react with С 1 -С 8 -alkylhydrazines along two routes giving mixtures of 1-R'-3-R-and 1-R'-5-R-pyrazoles with the prevalence of 1,3-isomer. The proportion of 3-substituted 1-alkylpyrazole in the isomers mixture grows from 60 to 94-97% with growing length of the alkyl chain in the hydrazine. The alkylation of 1-unsubstituted 3(5)-alkylpyrazoles with alkyl bromides afforded predominantly (by 16-50%) 1,3-disubstituted pyrazoles. 1,3-Dialkyl-5-chloropyrazoles form from 2,2-dichlorovinyl alkyl ketones and functionalized alkylhydrazines. It was suggested to synthesize 1,3-dialkyl-substituted pyrazoles by dechlorination of unsymmetrically substituted 1,3-dialkyl-5-chloropyrazoles in the presence of complex nickel catalyst and water as the proton source.

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Section: (5)-ethyl- Propyl- and Butylpyrazolessupporting

confidence: 67%

Ratio of 1,3- and 1,5-dialkyl-substituted pyrazoles obtained from chlorovinyl alkyl ketones and alkylhydrazines, 3(5)-pyrazoles and alkyl bromides

et al. 2014

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“…The structure of chlorovinyl ketone I shows that the way of the formation of dichloromethyl 2-chlorovinyl ketone [2] which we have suggested before, from chloroacetyl chloride and 1,2-dichloroethylene, in this process does not exist.…”

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confidence: 85%

“…Under similar conditions [1][2][3][4] the reaction of 2-chlorobutanoyl chloride with the industrial mixture of cis-and trans-isomers of 1,2-dichloroethylene takes two routes. As a result formerly unknown 1,1-dichloropropyl 2-chlorovinyl ketone (I) and expected 1-chloropropyl 1,2,2-trichloroethyl ketone (II), and the produvct of the thermal dehydrochlorination of the latter, 1-chloropropyl 1,2-dichlorovinyl ketone (III) were obtained.…”

mentioning

confidence: 94%

“…We recently [1,2] established that the reaction of chloroacetyl chloride with 1,2-dichloroethylene in the presence of AlCl 3 took an unexpected route giving dichloromethyl 2-chlorovinyl ketone in 74% yield. The reaction of 2-chloropropionyl chloride with the same chloroethene proceeded in two directions [3]: with the generation as the main product of monochlorovinyl ketone, 1,1-dichloroethyl 2-chlorovinyl ketone (yield 49%), and also with the formation of 1-chloroethyl 1,2,2-trichloroethyl ketone and of the produvct of the thermal dehydrochlorination of the latter, 1-chloroethyl 1,2-dichlorovinyl ketone in a significantly lesser yield (~15%).…”

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confidence: 99%

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