Synthesis and reactivity of 3-methylene-7-vinylidenebicyclo(3. 3. 1)nonane

Journal Article · Sat May 10 00:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6136679

Krasutskii, P A; Fokin, A A; Yurchenko, A G

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), Vol. 21:12; Other Information: Translated from Zh. Org. Khim.; 21: No.12, 2522-2526(Dec 1985)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
DIENES
ACTIVATION ENERGY
DEHYDROCYCLIZATION
ISOMERIZATION
NMR SPECTRA
SYNTHESIS
ADAMANTANE
ALLENE
ARGON
BROMINE
CARBON TETRACHLORIDE
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL SHIFT
CYCLOALKANES
ENERGY-LEVEL TRANSITIONS
EUROPIUM COMPLEXES
HYDROCHLORIC ACID
INFRARED SPECTRA
IODINE
KETONES
PROTONS
SILVER COMPLEXES
SILVER NITRATES
SOLVATION
SULFURIC ACID
VIBRATIONAL STATES
ALKANES
BARYONS
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
COMPLEXES
ELEMENTARY PARTICLES
ELEMENTS
ENERGY
ENERGY LEVELS
EXCITED STATES
FERMIONS
FLUIDS
GASES
HADRONS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENS
HYDROCARBONS
HYDROGEN COMPOUNDS
INORGANIC ACIDS
NITRATES
NITROGEN COMPOUNDS
NONMETALS
NUCLEONS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
POLYENES
RARE EARTH COMPLEXES
RARE GASES
SILVER COMPOUNDS
SPECTRA
TRANSITION ELEMENT COMPLEXES
TRANSITION ELEMENT COMPOUNDS
400201* - Chemical & Physicochemical Properties