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

Journal Article · Sat May 10 04:00:00 UTC 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), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:12; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

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