2-chlorovinyl 1,1-dichloroethyl ketone from 2-chloropropionyl chloride and 1,2-dichloroethene

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

“…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.…”

New example of uncommon reaction of 2-chloroalkanoyl chlorides with dichloroethylene

“…We isolated 16% of ketone III, bp 92-95°С (3 mm Hg). 1 Н NMR spectrum (СDCl 3 ), δ, ppm: 1.04 t (3Н, CH 3 , 3 J 6.8 Hz), 1.94, 2.08 m (2Н, СН 2 , 3 J 8.5 Hz), 4.84 t (1Н, CHСl, 3 1 Н and 13 С NMR spectra were registered on a spectrometer Bruker DPX-400 (400.13 and 100.61 MHz respectively), internal reference HMDS.…”

“…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.…”

“…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%). Yet it is known [4,5] that under similar conditions from aliphatic carboxylic acids chlorides and dichloroacetyl chloride and 1,2-dichloroethylene formed alkyl and dichloromethyl 1,2-dichlorovinyl ketones.…”