Tautomerism in the series of methyl 5,5-dimethyl-2,4-dioxohexanoate acylhydrazones

Journal Article · Thu Jul 10 00:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6136867

Yakimovich, S I; Nikolaev, V N; Zerova, I V

It was shown by PMR spectroscopy that methyl 5,5-dimethyl-2,4-dioxohexanoate acylhydrazones exist in solutions as mixtures of the geometric isomers of the hydrazone and cyclic 5-hydroxypyrazoline forms. In the series of aroylhydrazones the introduction of electron-withdrawing substituents into the aromatic ring of the N-aroyl radical shifts the ring-chain equilibrium slightly toward the 5-hydroxypyrazoline tautomer. In the series of products from condensation with the hydrazides of aliphatic acids increase in the size of the substituent in the acyl part favors the open-chain hydrazone form.

• Research Organization: A.A. Zhdanov Leningrad State Univ., USSR
• OSTI ID: 6136867
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:2; ISSN JOCYA
• 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
AZOLES
BARYONS
BINDING ENERGY
CHEMICAL BONDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CONFORMATIONAL CHANGES
DEHYDROCYCLIZATION
DEUTERIUM COMPOUNDS
DMSO
ELECTRON DENSITY
ELECTRON TRANSFER
ELECTRONIC STRUCTURE
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
EQUILIBRIUM
FERMIONS
HADRONS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDRAZIDES
HYDRAZONES
HYDROGEN COMPOUNDS
HYDROGEN TRANSFER
HYDROXY COMPOUNDS
HYPERFINE STRUCTURE
ISOMERIZATION
ISOMERS
LEPTONS
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEONS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PROTONS
PYRAZOLES
PYRAZOLINES
SPECTRA
STEREOCHEMISTRY
SULFOXIDES
VALENCE