Chemistry of enol ethers. LXXXIV. Condensation of acetals of saturated aldehydes with 2-trimethylsilyloxy-1,3-dienes. Synthesis of /beta/-alkoxy-alkyl vinyl and divinyl ketones

Journal Article · Wed Nov 09 23:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5950368

Makin, S M; Nazarova, O N; Dymshakova, G M; Kundryutskova, L A

The addition of the acetals of saturated aldehydes (formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, and isobutyraldehyde) to 2-trimethylsilyloxy-4-methyl-1,3-pentadiene in the presence of aprotic acids (ZnCl/sub 2/, ZnBr/sub 2/, FeCl/sub 3/, SnCl/sub 4/, BF/sub 3/ /times/ OEt/sub 2/) takes place at positions 1, 2 of the diene system with the formation of /beta/-alkoxyalkyl vinyl ketones. The most effective catalysts of this reaction were stannic chloride and zinc bromide. The alkyl derivatives of divinyl ketones are formed when the obtained /beta/-alkoxyalkyl vinyl ketones are heated with p-toluenesulfonic acid.

• Research Organization: M.V. Lomonosov Moscow Institute of Fine Chemical Technology (USSR)
• OSTI ID: 5950368
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:6; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETALDEHYDE
ACETALS
ALDEHYDES
BORON COMPOUNDS
BORON FLUORIDES
BROMIDES
BROMINE COMPOUNDS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CHROMATOGRAPHY
COMPARATIVE EVALUATIONS
DEHYDROCYCLIZATION
DIENES
ETHERS
FLUORIDES
FLUORINE COMPOUNDS
FORMALDEHYDE
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
INFRARED SPECTRA
IRON CHLORIDES
IRON COMPOUNDS
KETONES
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
POLYENES
SEPARATION PROCESSES
SPECTRA
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
TIN CHLORIDES
TIN COMPOUNDS
TIN HALIDES
TRANSITION ELEMENT COMPOUNDS
ULTRAVIOLET SPECTRA
ZINC BROMIDES
ZINC CHLORIDES
ZINC COMPOUNDS
ZINC HALIDES