Reaction of alkane- and arenesulfonamides with allylic electrophiles, catalyzed by transition-metal complexes

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

OSTI ID:7159931

Kunakova, R V; Sirazova, M M; Dzhemilev, U M

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), Vol. 23:4; Other Information: Translated from Zh. Org. Khim.; 23: No. 4, 826-833(Apr 1987)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
ALKANES
HETEROGENEOUS CATALYSIS
NMR SPECTRA
AROMATICS
CHROMIUM COMPOUNDS
CATALYTIC EFFECTS
COBALT COMPOUNDS
COPPER COMPOUNDS
NICKEL COMPOUNDS
PALLADIUM COMPOUNDS
SULFONAMIDES
ZIRCONIUM COMPOUNDS
ALCOHOLS
AMINES
CARBON 13
CATALYSTS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
COMPARATIVE EVALUATIONS
COUPLING CONSTANTS
ESTERS
ETHERS
HYDROGEN 1
J-J COUPLING
SULFONES
VALENCE
AMIDES
ANTI-INFECTIVE AGENTS
ANTIMICROBIAL AGENTS
CARBON ISOTOPES
CATALYSIS
COUPLING
DRUGS
EVEN-ODD NUCLEI
HYDROCARBONS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOTOPES
KINETICS
LIGHT NUCLEI
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
REACTION KINETICS
SPECTRA
STABLE ISOTOPES
TRANSITION ELEMENT COMPOUNDS
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory