Thermolysis of cis- and trans-1,2-dideuteriocyclobutane
Journal Article
·
· J. Org. Chem.; (United States)
The synthesis and stereochemistry of thermolysis of cis- and trans-1,2-dideuteriocyclobutane is reported and the results are compared to previously calculated models of tetramethylene. Cis-trans isomerization of dideuterio-cyclobutane and complete cis-trans isomerization of ethylene-d/sub 2/ were observed. The fragmentation/isomerization ratio of 3.0 obtained at low fractional isomerization is consistent with a potential energy surface for tetramethylene, which is symmetric with regards to fragmentation and recombination. The rapid methylene rotation necessary to explain the observed stereochemical features of the reaction also limits the magnitude of the through-bond coupling interaction to a value comparable to the magnitude of the potential energy well. 1 figure, 8 tables.
- Research Organization:
- Univ. of Missouri, St. Louis
- OSTI ID:
- 6428841
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 44:5; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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OSTI ID:7076492
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OSTI ID:464850
Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
400303 -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALKANES
ALKENES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
COMPARATIVE EVALUATIONS
CYCLOALKANES
DATA
DATA FORMS
DECOMPOSITION
DEUTERIUM
DEUTERIUM COMPOUNDS
ETHYLENE
EXPERIMENTAL DATA
FRAGMENTATION
HIGH TEMPERATURE
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFORMATION
INFRARED SPECTRA
ISOLATED VALUES
ISOMERIZATION
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLING
LIGHT NUCLEI
LOW PRESSURE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PRESSURE DEPENDENCE
PYROLYSIS
REACTION INTERMEDIATES
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
SYNTHESIS
TEMPERATURE DEPENDENCE
THERMOCHEMICAL PROCESSES
YIELDS
400302* -- Organic Chemistry-- Isotope Effects-- (-1987)
400303 -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALKANES
ALKENES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
COMPARATIVE EVALUATIONS
CYCLOALKANES
DATA
DATA FORMS
DECOMPOSITION
DEUTERIUM
DEUTERIUM COMPOUNDS
ETHYLENE
EXPERIMENTAL DATA
FRAGMENTATION
HIGH TEMPERATURE
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFORMATION
INFRARED SPECTRA
ISOLATED VALUES
ISOMERIZATION
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLING
LIGHT NUCLEI
LOW PRESSURE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PRESSURE DEPENDENCE
PYROLYSIS
REACTION INTERMEDIATES
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
SYNTHESIS
TEMPERATURE DEPENDENCE
THERMOCHEMICAL PROCESSES
YIELDS