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Regioselective catalytic addition of terminal acetylenes to methyl esters of 1-alkylcyclopropene-3-carboxylic acids

Journal Article · · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
OSTI ID:6357111
; ; ; ;
In a recent communication, they reported the selective addition of hydrogen halide and carboxylic acids as well as phenol at the C/sup 2/-C/sup 3/ bond of the three-membered ring of methyl esters of 1-alkylcyclopropene-3-carboxylic acids (I) catalyzed by CuCl leading to high yields of the methyl esters of 4-substituted 3-butenoic acids. In a continuation of this study, they investigated the catalytic reaction of (I) with terminal acetylenes and HCN, which may be considered weak CH-acids. Terminal acetylenes and HCN in the presence of CuCl add regioselectively as CH-acids to the unsaturated three-membered ring of methyl esters of 1-alkylcyclopropene-3-carboxylic acids to form the methyl esters of the corresponding 3-alken-5-ynoic acids or 4-cyano-3-alkyl-3-butenoic acids in yields up to 60%.
Research Organization:
N.D. Zelinskii Institute of Organic Chemistry, Moscow, USSR
OSTI ID:
6357111
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. 34:10; ISSN BACCA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKENES
ALKYNES
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID ESTERS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
CHLORIDES
CHLORINE COMPOUNDS
CHROMATOGRAPHY
COMPLEXES
COPPER CHLORIDES
COPPER COMPLEXES
COPPER COMPOUNDS
COPPER HALIDES
COUPLING
COUPLING CONSTANTS
CYANIDES
CYCLOALKENES
ESTERS
EVEN-ODD NUCLEI
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
HYDROCYANIC ACID
HYDROGEN COMPOUNDS
INFRARED SPECTRA
INORGANIC ACIDS
INTERMEDIATE COUPLING
ISOMERS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MASS SPECTRA
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEI
ORGANIC COMPOUNDS
PROPYLENE
SEPARATION PROCESSES
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
THIN-LAYER CHROMATOGRAPHY
TRANSITION ELEMENT COMPLEXES
TRANSITION ELEMENT COMPOUNDS
YIELDS