New rearrangement in the reaction of 1-aryl-1-(dimethylamino)-ethylenes with nitrosobenzenes. Molecular and crystal structure of N/sup 1/,N/sup 1/-dimethyl-N/sup 2/-phenyl-2-oxo(3-pyridyl)acetamidine
The reaction of aryleneamines Ar(NMe/sub 2/)C=CH/sub 2/ (Ar = Ph, 2-Py, 3-Py, 4-Py) with nitrosobenzenes p-RC/sub 6/H/sub 4/NO (R = H, Cl, Br, Me, MeO) in benzene or ether (20/sup 0/C) is accompanied by rearrangement and leads to N/sup 1/, N/sup 1/-dimethyl-N/sup 2/-aryl-2-oxo(aryl)-acetamidines (20-40%) and a mixture of products from reduction of the nitroso compounds. The effect of temperature on the yield of the amidines is insignificant, and the presence of one or two methyl groups at the ..beta.. position of the enamine leads to the formation of only azoxybenzene. Accepting substituents in the nitrosobenzenes do not affect the yield of the rearrangement products, while donors reduce it. The reaction is accompanied by the formation of radical particles, and a reaction scheme is proposed. The acid hydrolysis of the obtained amidines and their reduction with lithium aluminum hydride were investigated.
- Research Organization:
- M.V. Lomonosov Moscow State Univ., USSR
- OSTI ID:
- 6286504
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:9; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
360602 -- Other Materials-- Structure & Phase Studies
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACID HYDROLYSIS
ALKALI METAL COMPOUNDS
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
AMIDINES
AMINES
AROMATICS
BENZENE
BOND ANGLE
BOND LENGTHS
CARBON 13
CARBON ISOTOPES
CATALYTIC EFFECTS
CHARGED PARTICLES
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHROMATOGRAPHY
COHERENT SCATTERING
CRYSTAL LATTICES
CRYSTAL STRUCTURE
DECOMPOSITION
DEUTERIUM COMPOUNDS
DIFFRACTION
DIMENSIONS
ELECTRON SPIN RESONANCE
ELECTRONIC STRUCTURE
ELEMENTS
ETHERS
EVEN-ODD NUCLEI
HALOGENS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROLYSIS
INFRARED SPECTRA
IODINE
IONIZATION
IONS
ISOTOPES
LATTICE PARAMETERS
LENGTH
LIGHT NUCLEI
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
LYSIS
MAGNETIC RESONANCE
MASS SPECTRA
MOLECULAR IONS
MOLECULAR STRUCTURE
MONOCLINIC LATTICES
MULTIPLETS
NITROSO COMPOUNDS
NMR SPECTRA
NONMETALS
NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REDUCTION
RESONANCE
SCATTERING
SEPARATION PROCESSES
SOLVOLYSIS
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
ULTRAVIOLET SPECTRA
X-RAY DIFFRACTION