Reaction of cis-bicyclo(4. 3. 0)nona-3,7-diene with iodine. Synthesis of tricyclo(4. 3. 0. 0/sup 3,7/)nona-4,8-diene (brexa-4,8-diene)

Journal Article · Mon Dec 19 23:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5950576

Lukovskaya, E V; Bobyleva, A A; Pekhk, T I; Dubitskaya, N F; Petrushenkova, I A; Belikova, N A

The reaction of iodine with cis-bicyclo(4.3.0)nona-3,7-diene is accompanied by regioselective and stereoselective transannular cyclization with the formation of endo-4,exo-8-diiodobrexane. Methods were developed for the production of endo-9-iodobrex-4-ene and brexa-4,8-diene with yields of 26 and 20% respectively. The mechanism of transannular cyclization is discussed.

• Research Organization: M.V. Lomonosov Moscow State Univ. (USSR)
• OSTI ID: 5950576
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:7; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
CARBON TETRACHLORIDE
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
CHROMATOGRAPHY
CRYSTALLIZATION
DEHYDROCYCLIZATION
DIENES
DMSO
DOUBLE BONDS
ELEMENTS
ENERGY
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATION
HALOGENS
HYDROCARBONS
IODINATION
IODINE
KINETICS
NMR SPECTRA
NONMETALS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC SOLVENTS
ORGANIC SULFUR COMPOUNDS
PHASE TRANSFORMATIONS
POLYENES
QUANTITY RATIO
REACTION KINETICS
SEPARATION PROCESSES
SOLVENTS
SPECTRA
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SULFOXIDES
SYNTHESIS
TEMPERATURE DEPENDENCE
YIELDS