Polyfluorinated. cap alpha. ,. beta. -unsaturated ketons

Journal Article · Thu Jul 10 04:00:00 EDT 1986 · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00952855· OSTI ID:6475997

Latypov, R R; Belogai, V D; Pashkevich, K I

The ..cap alpha..,..beta..-unsaturated ketones (..cap alpha..,..beta..-UK), particularly those groups containing fluoroalkyl groups, are of interest as highly reactive compounds having two nonequivalent electrophilic centers. In the present investigation, by boiling polyfluorinated aldehydes with methylketones in glacial acetic acid, they have obtained for the first time the polyfluorinated ..beta..-hydroxy-ketones, the dehydration of which has been used to synthesize the corresponding polyfluorinated ..cap alpha..,..beta..-UK, and their structure and reactions with the nucleophiles NH/sub 3/, PhNH/sub 2/, MeOH have been studied. In the PMR spectra of the ..cap alpha..,..beta..-UK (X)-(XVI) two doublets of triplets are observed at 6.9 and 7.9 ppm, caused by the spin-spin coupling of the olefin protons with the CF/sub 2/ group of the substituent. For ..cap alpha..,..beta..-UK, apart from the cis-trans isomerism relative to the C=C bond, a rotational isomerism is possible, caused by rotation around the C-C single bond. The presence in the IR spectra of absorption bands from nonplanar torsion-deformation vibrations of C-H for a double bond (nu = 975-980 cm/sup -1/) and the high value of the spin-spin coupling constant of the olefin protons (J/sub HH/ = 15 Hz) indicate unambiguously the transconfiguration of the olefin protons.

• Research Organization: Institute of Chemistry, Sverdlovsk, USSR
• OSTI ID: 6475997
• Journal Information: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 35:1; ISSN BACCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALDEHYDES
ALKENES
BINDING ENERGY
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
COUPLING
COUPLING CONSTANTS
ELECTRON SPIN RESONANCE
ENERGY
FLUORINATION
HALOGENATION
HYDROCARBONS
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
J-J COUPLING
KETONES
LATTICE VIBRATIONS
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
RAMAN SPECTRA
RESONANCE
SPECTRA
SYNTHESIS
YIELDS