Reaction of alkane- and arenesulfonamides with allylic electrophiles, catalyzed by transition-metal complexes
The reactions of N-methyl-, N-phenyl-, N-amyl-, and N-allyl-p-toluenesulfonamides and the corresponding butanesulfonamides and also of unsubstituted p-toluenesulfonamide with allyl alcohols, ethers, esters, amines, sulfides, and sulfones, catalyzed by the low-valence compounds of palladium nickel, iron, cobalt, zirconium, chromium, and copper and leading to difficultly obtainable N-alkenylsulfonamides with specific structures, were investigated. The complex catalysts based on compounds of nickel, iron, and copper activated with triphenylphosphine direct the reaction of N-methyltoluenesulfonamide with 2,7-octadienyl acetate toward the exclusive formation of N-methyl-N-(1,7-octadiene-3-yl)-p-toluenesulfonamide, while the phosphine complexes of palladium direct the reaction toward N-methyl-N-(2,7-octadienyl)-p-toluenesulfonamide. The ..pi..-allyl complexes of palladium, containing the sulfonamide molecules in the coordination sphere of the central atom of the catalyst, promote the isomerization of 2,7-octadienyl acetate to the branched 1,7-isomer.
- Research Organization:
- Institute of Chemistry, Ufa (USSR)
- OSTI ID:
- 7159931
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:4; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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74 ATOMIC AND MOLECULAR PHYSICS
ALCOHOLS
ALKANES
AMIDES
AMINES
ANTI-INFECTIVE AGENTS
ANTIMICROBIAL AGENTS
AROMATICS
CARBON 13
CARBON ISOTOPES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
CHROMIUM COMPOUNDS
COBALT COMPOUNDS
COMPARATIVE EVALUATIONS
COPPER COMPOUNDS
COUPLING
COUPLING CONSTANTS
DRUGS
ESTERS
ETHERS
EVEN-ODD NUCLEI
HETEROGENEOUS CATALYSIS
HYDROCARBONS
HYDROGEN 1
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOTOPES
J-J COUPLING
KINETICS
LIGHT NUCLEI
NICKEL COMPOUNDS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PALLADIUM COMPOUNDS
REACTION KINETICS
SPECTRA
STABLE ISOTOPES
SULFONAMIDES
SULFONES
TRANSITION ELEMENT COMPOUNDS
VALENCE
ZIRCONIUM COMPOUNDS