76003-54-8Relevant academic research and scientific papers
Phosphonothioate hydrolysis by molybdocene dichlorides: Importance of metal interaction with the sulfur of the thiolate leaving group
Kuo, Louis Y.,Baker, Devon C.,Dortignacq, Adria K.,Dill, Kristina M.
, p. 4759 - 4765 (2013/09/24)
The metallocene bis(cyclopentadienyl)molybdenum(IV) dichloride Cp 2MoCl2 hydrolyzes O,S-diethyl phenylphosphonothioate (1) with only P-S scission to yield a phosphonate under mild aqueous conditions. In terms of degrading phosphonoth
Stereochemical inversion of phosphonothioate methanolysis by La(III) and Zn(II): Mechanistic implications for the degradation of organophosphate neurotoxins
Kuo, Louis Y.,Glazier, Sara K.
experimental part, p. 328 - 335 (2012/03/12)
The utility of phosphonothioate methanolysis to degrade organophosphate neurotoxins has prompted the stereochemical investigation of this useful transformation. The methanolysis of enantiomerically pure O,S-diethyl phenylphosphonothioate (5) was studied b
Kinetic Facial Selectivity in Nucleophilic Displacements at Tetracoordinate Phosphorus: Kinetics and Stereochemistry in the Reaction of Sodium Ethoxide with O,S-Dimethyl Phenylphosphonothioate
DeBruin, Kenneth E.,Tang, Chen-lan W.,Johnson, David M.,Wilde, Ronnie L.
, p. 5871 - 5879 (2007/10/02)
The reaction of ethoxide ion with O,S-dimethyl phenylphosphonothioate (1a) proceeds with competitive displacements of the methylthio and methoxy ligands.Each displacement occurs with complete inversion of configuration.The two products, ethyl methyl pheny
SILICON-PHOSPHORUS ANALOGIES. PARTICIPATION OF EXTERNAL NUCLEOPHILES TO ACTIVATED PROCESSES OF RACEMIZATION AND HYDROLYSIS OF CHLOROPHOSPHONO DERIVATIVES
Corriu, R. J. P.,Lanneau, G. F.,Leclercq, D.
, p. 1617 - 1626 (2007/10/02)
Kinetic and stereochemical studies show nucleophilic assistance by dimethylformamide (DMF), dimethylacetamide (DMA), hexamethylphosphotriamide (HMPT) and N-methylimidazole (NMI) in racemization and solvolysis of menthylchloro(phenyl)phosphonate, 1a, and O-ethylchloro(phenyl)thiophosphonate, 2.Similar orders of nucleophilic reactivity (Nu = NMI >> HMPT > DMF> DMA), and identical rate laws (vrac = k 2 and vH2O = k') are consistent with a common mechanism, governed by entropy (-60 u.e/= -40 u.e.).Analogies between reaction mechanisms at silicon and phosphorus are clearly evidenced.A two step process, involving rate-determining attack on a pentacoordinate complex is discussed.
