Chemistry of enol ethers. LXXVII. Synthesis of acetals of phenyl-substituted glutaconaldehydes

Journal Article · Sat Oct 10 04:00:00 EDT 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7159962

Makin, S M; Kruglikova, R I; Lonina, N N

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), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:5; ISSN JOCYA
• Country of Publication: United States
• Language: English

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
ACETALS
ACETONE
ACETOPHENONE
ACID HYDROLYSIS
ACTIVATION ENERGY
ALCOHOLS
ALDEHYDES
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
DECOMPOSITION
DEHYDROCYCLIZATION
DEUTERIUM COMPOUNDS
DIENES
ENERGY
ENOLS
ETHERS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROLYSIS
HYDROXY COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
KETONES
LIGHT NUCLEI
LYSIS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
POLYENES
SOLVOLYSIS
SPECTRA
STABLE ISOTOPES
SYNTHESIS
ZINC CHLORIDES
ZINC COMPOUNDS
ZINC HALIDES