61470-40-4Relevant academic research and scientific papers
Hydrolysis and alcoholysis of phosphinates and phosphonates
Harsági, Nikoletta,Keglevich, Gy?rgy,Sz?ll?si, Betti,Varga, Petra Regina
, (2021/11/04)
Phosphinic and phosphonic acids useful intermediates and biologically active compounds may be prepared from their esters: phosphinates and phosphonates, respectively, by acid-catalyzed hydrolysis either on conventional heating or on MW irradiation. The transesterification of alkyl phosphinates took place only in the presence of suitable ionic liquids as the catalysts. In the cases of phenylphosphonates, depending on the nature of the ionic liquid, the formation of the ester was accompanied by the fission of the C–O bond.
Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
Harsági, Nikoletta,Rádai, Zita,Szigetvári, áron,Kóti, János,Keglevich, Gy?rgy
, (2020/09/04)
The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The fission of the second P-O-C bond was found to be the rate-determining step.
Synthesis of biologically active 1-arylethylphosphonates
Gulyukina,Dolgina,Bondarenko,Beletskaya,Bondarenko,Henry,Lavergne,Ratovelomanana-Vidal,Genet
, p. 573 - 587 (2007/10/03)
A convenient and inexpensive general preparation method for 1-arylethylphosphonic acids and their esters was developed involving in reduction of the corresponding 1-ethenylphosphonates by ammonium formate in the presence of palladium on carbon. A homogeneous enantioselective hydrogenation of 1-arylethenylphosphonic acids in the presence of chiral ruthenium catalysts provided optically active 1-arylethylphosphonic acids of enantiomeric purity up to 86%. The preliminary data on biological activity testing of the 1-arylethylphosphoic acids synthesized evidence that some among the compounds obtained are low-toxic substances with the properties of immunosuppressors of the central type of action.
A practical synthetic approach to chiral α-aryl substituted ethylphosphonates
Goulioukina, Natalia S.,Dolgina, Tat'yana M.,Beletskaya, Irina P.,Henry, Jean-Christophe,Lavergne, Damien,Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre
, p. 319 - 327 (2007/10/03)
A convenient general method is reported for the synthesis of α-aryl substituted ethylphosphonic acids and esters by hydrogenation of α-aryl substituted ethenylphosphonic acids and esters. Racemic α-arylethylphosphonic acids and esters were prepared in 70-88% yield under palladium-assisted transfer hydrogenation conditions using ammonium formate. Asymmetric hydrogenation of α-arylethenylphosphonic acids using chiral Ru(II) catalysts led to α-arylethylphosphonic acids with enantiomeric excesses up to 86%.
Stereospecificity in the Rearrangement Reactions of an N-Phosphinoyl-O-sulfonylhydroxylamine with Methylamine and tert-Butylamine: Retention of Configuration at Phosphorus as Evidence for the Initial Formation of a Phosphonamidic Sulfonic Mixed Anhydride
Harger, Martin J. P.,Sreedharan-Menon, Ramesh
, p. 3261 - 3268 (2007/10/02)
Reaction of the N-phosphinoyl-O-sulfonylhydroxylamine PhMeCH(Ph)P(O)NHOMs 10 with RNH2 (R = Me or t-Bu) results in migration of the phenyl group from phosphorus to nitrogen which leads to the rearrangement product PhMeCHP(O)(NHPh)NHR.Using samples of 10 e
