Investigation of the decomposition of 1,3-diaryl-5-(3-chloro-2-quinoxalyl)-formazans by PMR and mass spectrometry
In contrast to triarylformazans, 1,3-diaryl-5-(3-chloro-2-quinoxalyl(formazans are unstable in ordinary organic solvents. When they are heated in chloroform, they undergo acidic cleavage, which leads to the formation of 3-chloro-2-quinoxalylhydrazones of p-substituted benzaldehydes and arenediazonium cations. These compounds, as a result of a redox reaction with the participation of the solvent, are converted to 4-chloro-1-(4-Y-phenyl)-1,2,4-triazolo(4,3-a)quinoxalines, substituted benzenes, nitrogen, and hydrogen chloride. The formation of the latter transforms the entire decomposition process into an autocatalytic process. Effects of chemical polarization of the nuclei (CPN), which unambiguously indicate the intermediate formation of diazoaryl radicals during the process, are observed in the PMR spectra of the final products. Such CPN effects, which were also observed in dimethyl sulfoxide (DMSO) and glacial acetic acid, indicate a process involving the oxidative formation of annelated triazoles from ..cap alpha..-azahetarylhydrazones via a radical pathway within a solvent cage.
- Research Organization:
- All-Union Scientific-Research Institute of Chemical Reagents and Ultrapure Chemical Substances, Moscow, USSR
- OSTI ID:
- 6084849
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 21:3; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACETIC ACID
ALDEHYDES
AROMATICS
AZAARENES
AZINES
AZOLES
BENZALDEHYDE
BENZENE
CARBON 13
CARBON ISOTOPES
CARBON TETRACHLORIDE
CARBOXYLIC ACIDS
CATALYSIS
CHARGED PARTICLES
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
DECOMPOSITION
DISSOCIATION
ELEMENTS
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDRAZONES
HYDROCARBONS
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYPERFINE STRUCTURE
INORGANIC ACIDS
INTERMEDIATE COUPLING
IONIZATION
IONS
ISOTOPES
J-J COUPLING
KINETICS
LIGHT NUCLEI
MASS SPECTRA
MOLECULAR IONS
MONOCARBOXYLIC ACIDS
NITROGEN
NMR SPECTRA
NONMETALS
NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
OXIDATION
PYRIDINES
QUINOLINES
RADICALS
REACTION KINETICS
SOLVENTS
SPECTRA
STABLE ISOTOPES
TEMPERATURE EFFECTS
TRIAZOLES
YIELDS