Reduction of 2-vinyl-1,1-bis(bromomethyl)cyclopropane
A study was carried out on the reduction of 2-vinyl-1,1-bis(bromomethyl)cyclopropane by various methods including electrochemical procedures. The major reaction pathways entail opening and expansion of the cyclopropane ring, while the product of the formation of a second three-membered ring, namely, vinylspiropentane, is formed in low yield. The probable radical mechanism for this reaction is discussed. Alkylation of diethyl malonate by trans-1,4-dibromo-2-butene using potassium carbonate as the base in absolute ethanol leads to the formation of diester in 63% yield. The use of the K/sub 2/CO/sub 3/-DMSO system, in contrast to the authors previous results, leads to the formation of desired product in yields from 5 to 10%. The reduction of diester by lithium aluminum hydride in ether gives 2-vinyl-1,1-bis(hydroxymethyl)cyclopropane in 84% yield.
- Research Organization:
- M.V. Lomonosov Moscow State Univ. (USSR)
- OSTI ID:
- 6007627
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:10; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
ALKALINE EARTH METAL COMPOUNDS
ALKANES
ALKENES
ALKYLATION
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
BROMINATED ALIPHATIC HYDROCARBONS
BUTENES
CARBON COMPOUNDS
CARBONATES
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINE COMPOUNDS
CHROMATOGRAPHY
CYCLOALKANES
DEHYDROCYCLIZATION
DICARBOXYLIC ACIDS
DMSO
ELECTRON TRANSFER
ESTERS
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
KINETICS
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
LITHIUM PERCHLORATES
MAGNESIUM COMPOUNDS
MALONIC ACID
NMR SPECTRA
ORGANIC ACIDS
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PERCHLORATES
POTASSIUM CARBONATES
POTASSIUM COMPOUNDS
REACTION KINETICS
REDUCTION
SEPARATION PROCESSES
SODIUM COMPOUNDS
SPECTRA
SULFOXIDES
YIELDS
ZINC COMPOUNDS