Reactions of aromatic nitro compounds. LVI. Reaction of polynitrodiphenyl sulfones with acetone and potassium hydroxide (in Russian)
The Yanovskii sigma complexes of 2,4-dinitrophenyl sulfone and 2,4-dinitro-, 2,4,4'-trinitro-, and 2,2',4,4'-tetranitrodiphenylsulfones were obtained and isolated in the crystalline form. It was established by PMR, IR, and electronic spectroscopy that they are all products from addition of the acetone residue to the fifth carbon atom of the dinitro-substituted ring; in contrast to polynitrodiphenyl sulfides, the isomeric adducts at the C/sup 3/ atom are not formed. Compared with the analogous complexes of sulfides, the synthesized products possess enhanced thermodynamic stability in an acetone-methanol medium. In DMSO they are rapidly decomposed by traces of water to dinitrophenolate and the corresponding arenesulfinic acids. The decomposition of the methyl dinitrophenyl sulfone complex takes place with preferential substitution of the para-nitro group and the formation of methyl 2-nitro-4-hydroxyphenyl sulfone.
- Research Organization:
- L. N. Tolstoi Tul'sk State Pedagogical Institute, USSR
- OSTI ID:
- 6388441
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:6; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- Russian
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Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACETONE
ACTIVATION ENERGY
ALCOHOLS
ALKALI METAL COMPOUNDS
AROMATICS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
COMPLEXOMETRY
COUPLING
COUPLING CONSTANTS
DECOMPOSITION
DEUTERIUM COMPOUNDS
DMSO
ENERGY
ENERGY LEVELS
EXCITED STATES
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
J-J COUPLING
KETONES
LINE WIDTHS
METHANOL
MOLECULAR STRUCTURE
MULTIPLETS
NITRO COMPOUNDS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PHENOLATES
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
SPECTRA
SPECTRAL SHIFT
STABILITY
SULFONES
SULFOXIDES
SYNTHESIS
VIBRATIONAL STATES