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Reaction of 3-(2,2,2-trichloroethylidene)-2,4-pentanedione with zinc and acid chlorides

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6388397
; ;
It was established that 3-(2,2,2-trichloroethylidene)-2,4-pentanedione readily reacts with zinc in aprotic solvents with the formation of an organozinc compound which is stable under the reaction conditions. The organozinc compound is acylated by acid chlorides, giving 3-(2,2-dichlorovinyl)-4-acyloxy-3-penten-2-ones. It was shown that the use of HMPTA as solvent with triethylamine or pyridine as additives significantly increases the yield of the final reaction products. The configuration of the synthesized compounds was studied by PMR, and it was found that they are formed as mixtures of Z and E isomers.
Research Organization:
A.M. Gor'kii Perm State Univ., USSR
OSTI ID:
6388397
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:6; ISSN JOCYA
Country of Publication:
United States
Language:
English

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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
ACTIVATION ENERGY
ACYLATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE 35
CHLORINE ISOTOPES
COMPLEXES
COMPLEXOMETRY
COUPLING
COUPLING CONSTANTS
ELEMENTS
ENERGY
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
INORGANIC ACIDS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOMERS
ISOTOPES
J-J COUPLING
KETONES
LIGHT NUCLEI
METALS
MULTIPLETS
NMR SPECTRA
NUCLEAR QUADRUPOLE RESONANCE
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
RESONANCE
SPECTRA
STABLE ISOTOPES
SYNTHESIS
TEMPERATURE DEPENDENCE
YIELDS
ZINC
ZINC COMPLEXES