Synthesis and reactivity of 3-methylene-7-vinylidenebicyclo(3. 3. 1)nonane
The synthesis of 3-methylene-7-vinylidenebicyclo(3.3.1)nonane - a new representative of pseudoconjugated allenes - was realized. In its reaction with electrophilic reagents (sulfuric acid, hydrogen chloride, bromine, and iodine) preferential cyclization to derivatives of adamantane occurs. Increase in the sulfuric acid concentration leads to the formation of 1,2-dimethylprotoadamantan-3-one - the product from more extensive rearrangement. In addition to transannular cyclization, hydrogen chloride in hexane gives rise to exo-endo isomerization of the ..pi.. bond. The differences in the regioselectivity of transannular cyclization under the influence of the acid and the halogen are discussed.
- OSTI ID:
- 6136679
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:12; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ADAMANTANE
ALKANES
ALLENE
ARGON
BARYONS
BROMINE
CARBON TETRACHLORIDE
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
COMPLEXES
CYCLOALKANES
DEHYDROCYCLIZATION
DIENES
ELEMENTARY PARTICLES
ELEMENTS
ENERGY
ENERGY LEVELS
ENERGY-LEVEL TRANSITIONS
EUROPIUM COMPLEXES
EXCITED STATES
FERMIONS
FLUIDS
GASES
HADRONS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENS
HYDROCARBONS
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
INFRARED SPECTRA
INORGANIC ACIDS
IODINE
ISOMERIZATION
KETONES
NITRATES
NITROGEN COMPOUNDS
NMR SPECTRA
NONMETALS
NUCLEONS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
POLYENES
PROTONS
RARE EARTH COMPLEXES
RARE GASES
SILVER COMPLEXES
SILVER COMPOUNDS
SILVER NITRATES
SOLVATION
SPECTRA
SULFURIC ACID
SYNTHESIS
TRANSITION ELEMENT COMPLEXES
TRANSITION ELEMENT COMPOUNDS
VIBRATIONAL STATES