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:
- Lomonosov Moscow State Univ., Moscow (Russian Federation)
- OSTI ID:
- 6035664
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 22:1; Other Information: Translated from Zh. Org. Khim.; 22: No.1, 110-121(Jan 1986)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
ALKENES
NMR SPECTRA
SYNTHESIS
ALKYNES
CYCLOALKANES
LITHIUM COMPLEXES
CATALYTIC EFFECTS
ALKYLATION
BROMINATION
CARBON 13
CATALYSIS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
COUPLING CONSTANTS
DEHALOGENATION
DEHYDRATION
DEHYDROGENATION
DIENES
ETHYLENE
HYDROGEN TRANSFER
HYPERFINE STRUCTURE
INFRARED SPECTRA
ISOMERS
J-J COUPLING
MOLECULAR STRUCTURE
MULTIPLETS
PROPANE
PROTONS
REDUCTION
STEREOCHEMISTRY
ALKANES
BARYONS
CARBON ISOTOPES
CHEMICAL REACTIONS
COMPLEXES
COUPLING
ELEMENTARY PARTICLES
EVEN-ODD NUCLEI
FERMIONS
HADRONS
HALOGENATION
HYDROCARBONS
INTERMEDIATE COUPLING
ISOTOPES
KINETICS
LIGHT NUCLEI
NUCLEI
NUCLEONS
ORGANIC COMPOUNDS
POLYENES
REACTION KINETICS
SPECTRA
STABLE ISOTOPES
YIELDS
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory