Chemistry of enol ethers. LXXVII. Synthesis of acetals of phenyl-substituted glutaconaldehydes
The condensation of the acetals of acetophenone and acetaldehyde with enol ethers, as a result of which 2- and 3-phenyl-1,1,3-trialkoxybutanes were obtained, was studied. The acid hydrolysis of the products leads to the formation of 2- and 3-phenylbutenals, from which 2- and 3-phenyl-1-trimethylsilyloxy-1,3-butadienes were obtained by the action of trimethylchlorosilane and triethylamine. The reaction of the silyloxydienes with ethyl orthoformate in the presence of zinc chloride as catalyst gave the monoacetals of ..cap alpha..- and ..beta..-phenylglutaconaldehydes, which were converted into the corresponding bisacetals by the further action of the orthoformate. The /sup 1/H NMR spectra of 50% solutions of the substances being analyzed in deuterochloroform or deuteroacetone were recorded on Bruker WH-90 and Bruker WM-250 instruments at 90 and 250 MHz respectively.
- Research Organization:
- M. V. Lomonosov Moscow Institute of Fine Chemical Technology (USSR)
- OSTI ID:
- 7159962
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 23:5; Other Information: Translated from Zh. Org. Khim.; 23: No. 5, 938-944(May 1987)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
ACETALS
DEHYDROCYCLIZATION
ISOMERIZATION
NMR SPECTRA
SYNTHESIS
ZINC CHLORIDES
CATALYTIC EFFECTS
ACETONE
ACETOPHENONE
ACID HYDROLYSIS
ACTIVATION ENERGY
ALDEHYDES
CHEMICAL SHIFT
CHLOROFORM
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DIENES
ENOLS
ETHERS
HYDROGEN 1
INFRARED SPECTRA
J-J COUPLING
ORGANIC SILICON COMPOUNDS
ALCOHOLS
CHEMICAL REACTIONS
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
COUPLING
DECOMPOSITION
ENERGY
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROLYSIS
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOTOPES
KETONES
LIGHT NUCLEI
LYSIS
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYENES
SOLVOLYSIS
SPECTRA
STABLE ISOTOPES
ZINC COMPOUNDS
ZINC HALIDES
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory