Implicit nucleophilic reagents in the sulfur dioxide-amine system. Sulfur trioxide treatment of azomethines

Journal Article · Sun Mar 20 00:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5971073

Bodrikov, I V; Krasnov, V L; Matyukov, E V; Chernov, A N; Verin, I A

It was shown by x-ray crystallographic analysis that the products form the reaction of azomethines with the sulfur dioxide-methylamine system are methylammonium 1-aryl-1-(arylamino)methanesulfonates. In aqueous solutions of the latter the amine fragment is redistributed with the formation of arylammonium 1-aryl-1-(arylamino)methanesulfonates. It was established that all the obtained salts are in equilibrium with the azomethines in solutions. The form of the nucleophile taking part in the reaction with the azomethine is suggested on the basis of the data from the PMR spectra of the methylamine-sulfur dioxide system. It was established that in water at room temperature and, particularly, with acid catalysis the compounds undergo fragment transformations which lead finally to redistribution of the covalently bonded amine fragment between the anionic and cationic parts of the salt with the formation of arylammonium 1-aryl-1-(arylamino)methanesulfonates.

• Research Organization: A.A. Zhdanov Gor'kii Polytechnic Institute (USSR)
• OSTI ID: 5971073
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 23:10; Other Information: Translated from Zh. Org. Khim.; 23: No. 10, 2174-2180 (Oct 1987)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AZO COMPOUNDS
CATALYSIS
INORGANIC ACIDS
CATALYTIC EFFECTS
SULFONATES
STRUCTURAL CHEMICAL ANALYSIS
ACTIVATION ENERGY
AMINATION
AMMONIUM COMPOUNDS
AQUEOUS SOLUTIONS
CRYSTAL STRUCTURE
DEUTERIUM COMPOUNDS
HEAVY WATER
METHYLAMINE
METHYLATION
NMR SPECTRA
SULFONATION
SULFUR DIOXIDE
SULFUR TRIOXIDE
X-RAY DIFFRACTION
AMINES
CHALCOGENIDES
CHEMICAL REACTIONS
COHERENT SCATTERING
DIFFRACTION
DISPERSIONS
ENERGY
HYDROGEN COMPOUNDS
MIXTURES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
SCATTERING
SOLUTIONS
SPECTRA
SULFUR COMPOUNDS
SULFUR OXIDES
WATER
400201* - Chemical & Physicochemical Properties