55484-54-3Relevant articles and documents
Synthesis, structure, and characteristics of 1,2-dichlorovinyl alkyl ketones
Bozhenkov,Leckovskaya,Larina,Ushakov,Dolgushin,Mirskova
, p. 1583 - 1592 (2004)
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. 2004 MAIK "Nauka/Interperiodica".
Amidrazones. 14. The Formation of 1,1-Disubstituted Hydrazines from the Base-promoted Hydrolysis of 1,1-Disubstituted-3-amino-4,5-dihydro-1H-pyrazolium Halides: Mechanistic Considerations
Smith, Richard F.,Dennis, Lisa A.,Ryan, William J.,Rodriguez, George,Brophy, Keith A.
, p. 181 - 183 (2007/10/02)
Three mechanistic pathways are considered for the hydroxide-promoted conversion of 1,1-disubstituted-3-amino-4,5-dihydro-1H-pyrazolium halides 1 to 1,1-disubstituted hydrazines, ammonia and sodium 3-hydroxypropanoate.Evidence presented in this paper supports a hydrolysis mechanism c that is initiated by hydroxide ion addition to the 3-position of 1 to form a tetrahedral intermediate 7.