(3 + 2)-Cycloaddition of C,N-diarylnitrilimines to S,S-dialkyl esters of 1-phenylethenyldithiophosphonous acid
The authors have found that the replacement of alkoxyl groups by thioalkyl groups at the phosphorus atom in derivatives of 1-phenylethenylphosphonous acid radically alters the direction of their reactions with C,N-diarylnitrylimines. In the reaction of S,S-diethyl- and S,S-diisopropyl-1-phenylethenyldithiophosphonites with C-aryl-N-phenylnitrylimines, and dithiophosphonites emerge as dipolarophilic. As a result of classical (3 + 2)-cycloaddition, 1,3,5-triarylpyrazoles are obtained as the final products. The reaction probably proceeds through formation of unstable phosphorylated pyrazolines. In the PMR spectra, signals of vinyl protons are lacking, and there are two quartets characteristic of the CH/sub 2/ group in the pyrazolines, with delta 4.45-4.50 and 3.42-3.47 ppm and SSCC J (PH/sub A/) 7.8-8.0 Hz, J (PH/sub B/) 5.8-6.0 Hz, J (H/sub Z/H/sub B/) 18.0 Hz.
- Research Organization:
- Leningrad Technological Institute of the Cellulose and Paper Industry (USSR)
- OSTI ID:
- 7005175
- Journal Information:
- J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:5; ISSN JGCHA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
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Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACTIVATION ENERGY
AZOLES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
ENERGY
ESTERS
HETEROCYCLIC COMPOUNDS
IMINES
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
KINETICS
LIGHT NUCLEI
MULTIPLETS
NITRILES
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHOSPHONIC ACID ESTERS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
PYRAZOLES
REACTION KINETICS
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS