Degenerate rearrangement of 5-arylthio-1,2,3,4,5-pentamethyl-1,3-cyclopentadienes

Journal Article · Tue Oct 20 04:00:00 EDT 1987 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7199999

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

The authors have detected and studied a degenerate rearrangement in 5-Sr-1,2,3,4,5-pentamethyl-1,3-cyclopentadienes (R=Ph, C/sub 6/F/sub 5/), which is in all probability realized by a 1,2-shift of the SR group. Reversible broadening and fusion of the signals of the CH/sub 3/ groups, corresponding to the proposed mechanism, are observed in the PMR spectra in (CD/sub 3/)/sub 2/SO or in Ph/sub 2/O at 140-180/sup 0/C. The alternative mechanism of intermolecular migration of the migrant is rejected on the basis of the fact that the magnitude of the exchange broadening of the signals for the CH/sub 3/ groups in the PMR spectra of the dienes hardly changes at all with fivefold dilution of the solutions.

• Research Organization: Novosibirsk Institute of Organic Chemistry (USSR)
• OSTI ID: 7199999
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:5; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKENES
CHEMICAL REACTIONS
CHEMICAL SHIFT
CONFORMATIONAL CHANGES
COUPLING
COUPLING CONSTANTS
CYCLOALKENES
CYCLOPENTADIENE
DEUTERIUM COMPOUNDS
DIENES
DIPOLE MOMENTS
DMSO
FLUORINE 19
FLUORINE ISOTOPES
HYDROCARBONS
HYDROGEN COMPOUNDS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPE EFFECTS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
LINE BROADENING
MAGNETIC DIPOLE MOMENTS
MAGNETIC MOMENTS
MASS SPECTRA
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POLYENES
SPECTRA
STABLE ISOTOPES
SULFOXIDES