Mechanism of intramolecular cycloalkylation of 3-methyl-3-phenyl-1-butanol in the presence of D sub 3 PO sub 4
Journal Article
·
· Journal of Organic Chemistry of the USSR (English Translation); (USA)
OSTI ID:5523855
- A.A. Zhdanov Irkutsk State Univ. (USSR)
The intramolecular cycloalkylation of isomeric 2-methyl-4-phenyl-2-butanol and 3-methyl-3-phenyl-1-butanol in D{sub 3}PO{sub 4} is accompanied by hydrogen exchange with the formation of deuterated 1,1-dimethylindane. The distribution of the deuterium in the polymethylene ring shows that the reaction of the first alcohol takes place as a result of C{sub 5}-cyclization of the {gamma}-phenylalkyl cation, whereas the reaction of the second alcohol takes place by direct C{sub 5}-cyclization and by cyclization of the {gamma}-phenylalkyl cations formed as a result of 1,2- and 1,3-transfers of the phenyl group.
- OSTI ID:
- 5523855
- Journal Information:
- Journal of Organic Chemistry of the USSR (English Translation); (USA), Journal Name: Journal of Organic Chemistry of the USSR (English Translation); (USA) Vol. 24:8; ISSN 0022-3271; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALCOHOLS
ALKYLATION
BUTANOLS
CATALYTIC EFFECTS
CATIONS
CHARGED PARTICLES
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
DEUTERIUM
DEUTERIUM COMPOUNDS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
HYDROXY COMPOUNDS
INORGANIC ACIDS
IONS
ISOMERS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PHOSPHORIC ACID
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALCOHOLS
ALKYLATION
BUTANOLS
CATALYTIC EFFECTS
CATIONS
CHARGED PARTICLES
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
DEUTERIUM
DEUTERIUM COMPOUNDS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
HYDROXY COMPOUNDS
INORGANIC ACIDS
IONS
ISOMERS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PHOSPHORIC ACID
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS