Degenerate sigmatropic rearrangement of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene

Journal Article · Mon Feb 10 04:00:00 EST 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6033690

Borodkin, G I; Susharin, E R; Shakirov, M M; Shubin, V G

The kinetics of the degenerate rearrangement of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, realized by a 1,2-shift of a hydrogen atom, were studied by the labeled atom method and by dynamic PMR. The results from MINDO/3 quantum-chemical calculations are consistent with this mechanism. Linear correlations relating the rate of the 1,2-shifts of the hydrogen atom in the degenerate rearrangement of the carbocations and 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene to the parameters characterizing the skeleton of the rearrangement structures were obtained.

• Research Organization: Novosibirsk Institute of Organic Chemistry, USSR
• OSTI ID: 6033690
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:9; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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74 ATOMIC AND MOLECULAR PHYSICS
ACTIVATION ENERGY
ALKENES
ARRHENIUS EQUATION
ATOMIC MODELS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
COMPUTERIZED SIMULATION
CONFORMATIONAL CHANGES
CYCLOALKENES
CYCLOPENTADIENE
DEUTERIUM
DEUTERIUM COMPOUNDS
DIENES
ELECTRONIC STRUCTURE
ENERGY
EQUATIONS
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
ISOMERS
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LABELLING
LIGHT NUCLEI
LINE BROADENING
MATHEMATICAL MODELS
MECHANICS
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
POLYENES
QUANTUM MECHANICS
REACTION KINETICS
SIMULATION
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY