Stereochemistry of 2,4-dinitrophenylhydrazones of β,β-dichlorovinyl ketones

I. D. Kalikhman, G. G. Levkovskaya, L. I. Lavlinskaya, A. N. Mirskova, A. S. Atavin

Research output: Contribution to journalArticlepeer-review


1. It was shown by the PMR method that 2,4-dinitrophenylhydrazones of β,β-dichlorovinyl ketones exist in the form of a mixture of two stereoisomers (syn- and anti-forms), the ratio of which is determined by the steric and electronic structure of the C-substituent. 2. The equilibrium content of the syn- and anti-isomers can be changed directedly under chemical and photochemical influences. 3. For the aldehyde derivative the S-cisoid conformations of the molecule predominates. The same conformations is evidently characteristic of alkyl ketone derivatives, while aryl ketones exist in a S-transoid form. 4. The stereochemical peculiarities found for the compounds studied explain their behavior in reactions of cyclization to pyrazoles.

Original languageEnglish
Pages (from-to)2180-2184
Number of pages5
JournalBulletin of the Academy of Sciences of the USSR Division of Chemical Science
Issue number10
StatePublished - 1 Oct 1973
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry (all)


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