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Reaction of the trichloroethylidene derivatives of acetoacetic ester and acetylacetone with zinc in the presence of. cap alpha. -chloro ethers

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6035688
;
The reaction of ethyl 2-(2,2,2-trichloroethylidene)-3-oxobutyrate and 3-(2,2,2-trichloroethylidene)-2,4-pentanedione with zinc and ..cap alpha..-chloro ethers was studied. In ether and ethyl acetate the reaction leads to the products from C-alkylation of the intermediate zinc enolate, i.e., to ethyl 2-alkoxymethyl-2-(2,2-dichlorovinyl)-3-oxobutyrates and 3-alkoxymethyl-3-(2,2-dichlorovinyl)-2,4-pentanediones. In ether and HMPTA the 0-alkylation products ethyl 2-(2,2-dichlorovinyl)-3-(butoxymethoxy)-2-butenoate and 3-(2,2-dichlorovinyl)-4-(butoxymethoxy)-3-penten-2-one are formed preferentially in the E configuration.
Research Organization:
A.M. Gor'kii Perm State Univ., USSR
OSTI ID:
6035688
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:1; 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
ACETOACETIC ACID
ACETYLACETONE
ACTIVATION ENERGY
ALCOHOLS
ALKYLATION
BARYONS
BUTYRIC ACID
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSIS
CATALYTIC EFFECTS
CHELATING AGENTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
COMPLEXES
COMPLEXOMETRY
COUPLING
COUPLING CONSTANTS
ELEMENTARY PARTICLES
ENERGY
ENOLS
ESTERS
ETHERS
FERMIONS
HADRONS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROXY COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
J-J COUPLING
KETO ACIDS
KETONES
MOLECULAR STRUCTURE
MONOCARBOXYLIC ACIDS
NMR SPECTRA
NUCLEONS
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PROTONS
REAGENTS
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
ZINC CHLORIDES
ZINC COMPLEXES
ZINC COMPOUNDS
ZINC HALIDES