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Cyclopropyl-substituted methylenecyclopropanes in reactions with dihalogenocarbenes

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:5949468
; ; ; ; ; ;
It was shown by the method of competing reactions that substituents in the methylenecyclopropane fragment in cyclopropyl-substituted methylenecyclopropanes have a steric effect rather than an electronic effect on the reactivity of the double bond toward dichlorocarbene. The addition of dichlorocarbene to them takes place stereospecifically with the formation of substituted dichlorospiropentanes having the syn arrangement of the cyclopropyl groups and the substituent. Two isomeric spirans with a syn-anti ratio of 5:1 are formed from 1,1-dicyclopropyl-3-trimethylstannylmethylenecyclopropane. The dichlorocarbene was generated by the action of 50% sodium hydroxide or powdered potassium hydroxide on chloroform in the presence of catalytic amounts of triethylbenzylammonium chloride.
Research Organization:
M.V. Lomonosov Moscow State Univ. (USSR)
OSTI ID:
5949468
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:11; ISSN JOCYA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKALI METAL COMPOUNDS
ALKANES
AMINES
AMMONIUM CHLORIDES
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
CARBENES
CARBON 13
CARBON ISOTOPES
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
CHLOROFORM
COMPLEXES
CYCLOALKANES
DAYS LIVING RADIOISOTOPES
DEUTERIUM COMPOUNDS
ENERGY
EVEN-ODD NUCLEI
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
INTERMEDIATE MASS NUCLEI
INTERNAL CONVERSION RADIOISOTOPES
ISOMERIC TRANSITION ISOTOPES
ISOMERIZATION
ISOMERS
ISOTOPES
LIGHT NUCLEI
NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
QUATERNARY COMPOUNDS
RADICALS
RADIOISOTOPES
SODIUM COMPOUNDS
SODIUM HYDROXIDES
STABLE ISOTOPES
STEREOCHEMISTRY
TIN 117
TIN 119
TIN COMPLEXES
TIN ISOTOPES