Chemistry of enol ethers. LXXXVIII. Condensation of the tetraethylacetal of malonaldehyde with /beta/-substituted enol alkyl ethers

Journal Article · Thu Mar 10 00:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5949336

Makin, S M; Kruglikova, R I; Kharitonova, O V; Arshava, B M

The action of /beta/-substituted enol ethers on the tetraethylacetal of malonaldehyde gave the acetals of 1,5- and 1,7-dialdehydes. The nature of the substituent in the enol ether was found to affect the regioselectivity of the reaction: condensation with ethers containing an electron-withdrawing substituent leads to 1,5-dialdehyde acetals, while condensation with ethers containing a strong electron-donor substituent leads to 1,7-dialdehyde acetals. The condensation of malonaldehyde tetraethylacetal with /beta/-substituted enol alkyl ethers was carried out at room temperature in the presence of zinc chloride as catalyst.

• Research Organization: M.V. Lomonosov Moscow Institute of Fine Chemical Technology (USSR)
• OSTI ID: 5949336
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 23:10; Other Information: Translated from Zh. Org. Khim.; 23: No. 10, 2089-2093 (Oct 1987)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ACETALS
DEHYDROCYCLIZATION
ETHERS
ACTIVATION ENERGY
ZINC CHLORIDES
CATALYTIC EFFECTS
ALDEHYDES
BINDING ENERGY
CARBON 13
CATALYSIS
CATALYSTS
CHEMICAL REACTION YIELD
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
ELECTRONS
ENOLS
HYPERFINE STRUCTURE
J-J COUPLING
MALONIC ACID
NMR SPECTRA
THIN-LAYER CHROMATOGRAPHY
VALENCE
ALCOHOLS
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CHROMATOGRAPHY
COUPLING
DICARBOXYLIC ACIDS
ELEMENTARY PARTICLES
ENERGY
EVEN-ODD NUCLEI
FERMIONS
HALIDES
HALOGEN COMPOUNDS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOTOPES
LEPTONS
LIGHT NUCLEI
NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
SEPARATION PROCESSES
SPECTRA
STABLE ISOTOPES
YIELDS
ZINC COMPOUNDS
ZINC HALIDES
400201* - Chemical & Physicochemical Properties