Reaction of 3,7-divinylidenebicyclo(3. 3. 1)nonane with electrophilic reagents

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

OSTI ID:6387671

Krasutskii, P A; Fokin, A A; Kulik, N I; Yurchenko, A G

3,7-Divinylidenebicyclo(3.3.1)nonane reacts with electrophilic reagents (strong acids, halogens) with the formation of 3-substituted 1-vinyl-2-methyleneadamantanes. In the reaction with small amounts of hydrochloric acid isomerization of the exocyclic bond to an endocyclic bond is observed in parallel with transannular cyclization. Increase in the sulfuric acid concentration leads to more extensive rearrangement to a protoadamantanone derivative.

• Research Organization: Kiev Polytechnic Institute, USSR
• OSTI ID: 6387671
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 21:12; Other Information: Translated from Zh. Org. Khim.; 21: No.12, 2518-2522(Dec 1985)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
DIENES
DEHYDROCYCLIZATION
ISOMERIZATION
NMR SPECTRA
SYNTHESIS
ADAMANTANE
ALLENE
ATOMIC MODELS
BROMINE
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL REACTION YIELD
CHEMICAL SHIFT
COMPUTERIZED SIMULATION
CONFIGURATION INTERACTION
COUPLING CONSTANTS
CYCLOALKANES
ELECTRONIC STRUCTURE
EUROPIUM COMPLEXES
HYDROCHLORIC ACID
INFRARED SPECTRA
IODINE
J-J COUPLING
MULTIPLETS
PROTONS
QUANTUM MECHANICS
SILVER COMPLEXES
SULFURIC ACID
ALKANES
BARYONS
CHEMICAL REACTIONS
COMPLEXES
COUPLING
ELEMENTARY PARTICLES
ELEMENTS
FERMIONS
HADRONS
HALOGENS
HYDROCARBONS
HYDROGEN COMPOUNDS
INORGANIC ACIDS
INTERMEDIATE COUPLING
MATHEMATICAL MODELS
MECHANICS
NONMETALS
NUCLEONS
ORGANIC COMPOUNDS
POLYENES
RARE EARTH COMPLEXES
SIMULATION
SPECTRA
TRANSITION ELEMENT COMPLEXES
YIELDS
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory