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

Abstract

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.

Authors:
; ;
Publication Date:
Research Org.:
Institute of Chemistry, Ufa (USSR)
OSTI Identifier:
7159931
Resource Type:
Journal Article
Journal Name:
J. Org. Chem. USSR (Engl. Transl.); (United States)
Additional Journal Information:
Journal Volume: 23:4; Other Information: Translated from Zh. Org. Khim.; 23: No. 4, 826-833(Apr 1987)
Country of Publication:
United States
Language:
English
Subject:
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

Citation Formats

Kunakova, R V, Sirazova, M M, and Dzhemilev, U M. Reaction of alkane- and arenesulfonamides with allylic electrophiles, catalyzed by transition-metal complexes. United States: N. p., 1987. Web.
Kunakova, R V, Sirazova, M M, & Dzhemilev, U M. Reaction of alkane- and arenesulfonamides with allylic electrophiles, catalyzed by transition-metal complexes. United States.
Kunakova, R V, Sirazova, M M, and Dzhemilev, U M. 1987. "Reaction of alkane- and arenesulfonamides with allylic electrophiles, catalyzed by transition-metal complexes". United States.
@article{osti_7159931,
title = {Reaction of alkane- and arenesulfonamides with allylic electrophiles, catalyzed by transition-metal complexes},
author = {Kunakova, R V and Sirazova, M M and Dzhemilev, U M},
abstractNote = {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.},
doi = {},
url = {https://www.osti.gov/biblio/7159931}, journal = {J. Org. Chem. USSR (Engl. Transl.); (United States)},
number = ,
volume = 23:4,
place = {United States},
year = {Sun Sep 20 00:00:00 EDT 1987},
month = {Sun Sep 20 00:00:00 EDT 1987}
}