408316-47-2Relevant academic research and scientific papers
Aryl(dimethylaminomethyl)phosphinic Acid Esters: Syntheses, Structures, and Reactions with Halogen Hydrogen Acids, Tin Halides, and Trimethyl Halosilanes
Lutter, Michael,Jurkschat, Klaus
, p. 3481 - 3490 (2018/08/21)
This paper reports the synthesis of the aryl(iodomethyl)phosphinic acid ethyl esters, Ar(ICH2)P(O)OEt (Ar = Ph, Ar = mesityl), which, via dimethyamination, are converted to the corresponding aryl(dimethylaminomethyl)phosphinic acid ethyl esters, Ar(Me2NCH2)P(O)OEt (Ar = Ph, Ar = mesityl). Upon reaction with hydrogen chloride, compound Me2NCH2(Ph)P(O)OEt forms its hydrochloride salt as a crystalline material. Depending on the reaction conditions, treatment of Me2NCH2(Ph)P(O)OEt with SnCl2 gave either [Me2HNCH2(Ph)P(O)OEt][SnCl3] or the mixed-valent dinuclear tin salt [{Me2HNCH2(Ph)P(O)O}4SnCl2][SnCl3]2, as its dichloromethane solvate. The reaction of Me2NCH2(Mes)P(O)OEt with SiMe3I gives the diorgano bis(trimethylsiloxy)phosphinium iodide [Me2NCH2(Mes)P(OSiMe3)2]I, as its toluene solvate. In solution, it is involved in an equilibrium with Me2NCH2(Mes)P(O)OSiMe3 and SiMe3I. From the hydrolysis of [Me2NCH2(Mes)P(OSiMe3)2]I, the hydrogen iodide derivative [Me2HNCH2(Mes)P(O)OH]I was obtained as three different solvates. [Me2NCH2(Mes)P(OSiMe3)2]I reacted with SnF2 to give a product mixture from which the mixed-valent tin compound [{SnII2Me2NCH2(Mes)P(O)2}4SnIVF2]I2, was isolated. The compounds were characterized by NMR and IR spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction analysis.
Synthesis of a novel diarylphosphinic acid: A distorted ground state mimic and transition state analogue for amide hydrolysis
Schuman, Marc,Lopez, Xabier,Karplus, Martin,Gouverneur, Véronique
, p. 10299 - 10307 (2007/10/03)
We describe herein the synthesis of a new unsymmetrical diarylphosphinic acid, a hapten aimed to produce catalytic antibodies for the hydrolysis of heterocyclic amides. The phosphinate functionality was selected as a mimic both of the tetrahedral intermed
