Reactions of fluoroalkyl-. beta. -ketoesters with ammonia
It has been found that ..beta..-ketoesters containing highly fluorinated substituents (CF/sub 3/, or H(CF/sub 2/)/sub 4/) react with ammonia to give ..beta..-aminocrotonate esters, or under severe conditions, ..beta..-ketoamides. The latter react with a tenfold excess of ammonia to give ..beta..-aminocrotonamides together with acetamide and fluorocarboxamides. Acetoacetic and 4,4-difluoroacetoacetic esters react with ammonia, irrespective of the reaction conditions, to give ..beta..-aminocrotonate and 4,4-difluoro-..beta..-aminocrotonate esters. Using DNMR and dipole moments, it has been shown that rotation of the amino group around the C-N bond in fluorinated ..beta..-aminocrotonate esters is restricted (..delta..Gnumber approx. 50 kJ/mole).
- Research Organization:
- Institute of Chemistry, Sverdlovsk, USSR
- OSTI ID:
- 6417918
- Journal Information:
- Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Vol. 35:7; Other Information: Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; 35: No.7, 1586-1592(Jul 1986)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
ACETOACETIC ACID ESTERS
CHEMICAL REACTION KINETICS
AMMONIA
CARBOXYLIC ACID ESTERS
MAGNETIC DIPOLE MOMENTS
NMR SPECTRA
AMIDES
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
CROTONIC ACID
ELECTRON SPIN RESONANCE
FLUORINATION
HYPERFINE STRUCTURE
INFRARED SPECTRA
LINE BROADENING
NITROGEN 14
ORGANIC FLUORINE COMPOUNDS
QUADRUPOLE MOMENTS
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DIPOLE MOMENTS
ESTERS
HALOGENATION
HYDRIDES
HYDROGEN COMPOUNDS
ISOTOPES
KINETICS
LIGHT NUCLEI
MAGNETIC MOMENTS
MAGNETIC RESONANCE
MONOCARBOXYLIC ACIDS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NITROGEN ISOTOPES
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
REACTION KINETICS
RESONANCE
SPECTRA
STABLE ISOTOPES
YIELDS
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory