Synthesis of 1-substituted derivatives of pentacyclo(6,3,0. 0/sup 2,6/. 0/sup 3,10/. 0/sup 5,9/)-undecane (symmetrical trishomocubane)
During the action of boron tribromide on adamantanone and pentacyclo(6.3.0.0/sup 2,6/.0/sup 3,10/.0/sup 5,9/)undecane-4-one the carbonyl group is substituted by a dibromomethylene group. Protoadamantan-4-one is converted into 1,2-dibromoadamantane. The treatment of pentacyclo(5.4.0.0/sup 2,6/.0/sup 3,10/,0/sup 5,9)undecane-8,11-dione also leads to isomerization of the carbon skeleton of the molecule, and 7,7,11-tribromopentacycle(6.3.0.0/sup 2,6/,0/sup 3,10/,0/sup 5,9/)undecane-1-ol is formed. The latter served as the starting compound for the production of a series of 1-substituted derivatives of pentacyclo(6.3.0.0/sup 2,6/.0/sup 3,10/,0/sup 5,9/)undecane. 1-Hydroxypentacyclo(6.3.0.0/sup 2,6/,0/sup 3,10/,0/sup 5,9/)undecane is carbonylated by the Koch mechanism to pentacyclo(6.3.0.0/sup 2,6/0/sup 3,10/,0/sup 5,9/)undecane-1-carboxylic acid.
- Research Organization:
- Institute of Organic Chemistry, Kiev (USSR)
- OSTI ID:
- 7159876
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:4; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
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Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALCOHOLS
ALKANES
BORON BROMIDES
BORON COMPOUNDS
BROMIDES
BROMINATION
BROMINE COMPOUNDS
CARBONYLATION
CARBONYLS
CARBOXYLIC ACIDS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
FLUORINE 19
FLUORINE ISOTOPES
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HYDROCARBONS
HYDROFLUORIC ACID
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFRARED SPECTRA
INORGANIC ACIDS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
KETONES
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS