Diethyl vinylphosphonite in the Michael reaction

Journal Article · Thu Dec 10 04:00:00 EST 1987 · J. Gen. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:7169721

Trishin, Yu G; Peshkov, A F; Bondarenko, E A; Chistokletov, V N

The authors have found that diethyl vinylphosphonite, an analog of diethyl vinylphosphonate containing a tervalent phosphoruse atom, undergoes the Michael reaction. However, the addition of such typical addends as malonic and cyanoacetic esters goes with difficulty. Despite the variation of the reaction conditions, the yields of the adducts do not exceed 37%. Change in the reaction temperature from 20 to 80/sup 0/C, in the reactant ratio (of the vinylphosphonite to the addend) from 1:1 to 1:5, in the amount of catalyst (sodium ethoxide) from 0.3 to 1 mole, and in the reaction time to several days does not lead to the disappearance of the signal of diethyl vinylphosphonite in the /sup 31/P NMR spectrum (delta/sub p/ 157.5 ppm). The retention of more than one half of the diethyl vinylphosphonite in the unchanged state is evidenced also by GLC data. The compositions and structures of the compounds obtained were established on the basis of elemental analysis and IR, PMR, and /sup 31/P NMR spectroscopy.

• Research Organization: Leningrad Technological Institute of the Pulp and Paper Industry (USSR)
• OSTI ID: 7169721
• Journal Information: J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 57:6; ISSN JGCHA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ADDUCTS
ALKALI METAL COMPOUNDS
ALKOXIDES
AROMATICS
BENZENE
BUTYRIC ACID
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
DEUTERIUM COMPOUNDS
DICARBOXYLIC ACIDS
ENERGY
ESTERS
HYDROCARBONS
HYDROGEN COMPOUNDS
INFRARED SPECTRA
ISOMERIZATION
ISOTOPES
LIGHT NUCLEI
MALONIC ACID
MONOCARBOXYLIC ACIDS
MONOMERS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
SODIUM COMPOUNDS
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
VINYL MONOMERS
YIELDS