Synthesis of gem-disubstituted ethylene and acetylene derivatives of the cyclopropane series based on 1,1-diacylcyclopropanes
Methods for the conversion of 1,1-diacylcyclopropanes into gem-disubstituted dienes and acetylenes of the cyclopropene series were investigated: (a) reduction followed by dehydration of the diols; (b) conversion of the diketones into bistosylhydrazones and treatment of the latter with methyllithium; (c) dehydrohalogenation of gem-di(1-halogenoalkyl)cyclopropanes by the action of bases. Dehydration leads to intramolecular nucleophilic opening of the three-membered ring. 1,1-Divinylcyclopropanes and stereoisomeric 1,1-di(1-propenyl)cyclopropanes were obtained by two different methods, and the corresponding diynes and enynes were synthesized from them by bromination followed by dehydrobromination. 1,1-Di(1-propynyl)cyclopropane can be obtained by alkylation of 1,1-diethynyl-cyclopropane and also directly from 1,1-divinylcyclopropane without isolation of the intermediate 1,1-diethynylcyclopropane.
- Research Organization:
- M.V. Lomonosov Moscow State Univ., USSR
- OSTI ID:
- 6035664
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:1; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKANES
ALKENES
ALKYLATION
ALKYNES
BARYONS
BROMINATION
CARBON 13
CARBON ISOTOPES
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
COMPLEXES
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
DEHALOGENATION
DEHYDRATION
DEHYDROGENATION
DIENES
ELEMENTARY PARTICLES
ETHYLENE
EVEN-ODD NUCLEI
FERMIONS
HADRONS
HALOGENATION
HYDROCARBONS
HYDROGEN TRANSFER
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERS
ISOTOPES
J-J COUPLING
KINETICS
LIGHT NUCLEI
LITHIUM COMPLEXES
MOLECULAR STRUCTURE
MULTIPLETS
NMR SPECTRA
NUCLEI
NUCLEONS
ORGANIC COMPOUNDS
POLYENES
PROPANE
PROTONS
REACTION KINETICS
REDUCTION
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
SYNTHESIS
YIELDS