Isomerization of cis-2,4-dinitrostilbene in the presence of fluoride ion

Journal Article · Sat Nov 19 23:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6008908

Todres, Z V; Smirnov, V V; Sergeev, G B; Golubeva, E N; Ryapisov, S V

The reaction of cis-2,4-dinitrostilbene with potassium fluoride in the presence of 18-crown-6 in aprotic polar media takes place in two directions. The main direction is the reversible addition of the fluoride ion at the double bond, leading to the formation of trans-2,4-dinitrostilbene with a yield not lower than 90%. The fluoride ion enters the dinitrophenyl ring in parallel, and the fraction of this direction is not more than 10%. The obtained products were characterized as /sigma/ complexes of 2,4-dinitrostilbene.

• Research Organization: A.N. Nesmeyanov Institute of Heteroorganic Compounds, Moscow (USSR)
• OSTI ID: 6008908
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:6; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ABSORPTION SPECTRA
ACETONITRILE
ALCOHOLS
ALKALI METAL COMPOUNDS
AMIDES
AROMATICS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL EXPLOSIVES
CHEMICAL REACTIONS
COUPLING
COUPLING CONSTANTS
DMSO
EXPLOSIVES
FLUORIDES
FLUORINE COMPOUNDS
GLYCOLS
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOMERS
J-J COUPLING
NITRILES
NITRO COMPOUNDS
NITROMETHANE
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC POLYMERS
ORGANIC SULFUR COMPOUNDS
POLYETHYLENE GLYCOLS
POLYMERS
POTASSIUM COMPOUNDS
POTASSIUM FLUORIDES
SPECTRA
STILBENE
SULFOXIDES