18755-36-7Relevant articles and documents
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Bell,H.M.
, p. 681 - 685 (1969)
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Catalytic decomposition of simulants for chemical warfare V agents: Highly efficient catalysis of the methanolysis of phosphonothioate esters
Melnychuk, Stephanie A.,Neverov, Alexei A.,Brown, R. Stan
, p. 1767 - 1770 (2007/10/03)
(Chemical Equation Presented) As good as the original: Extremely effective methanolysis of phosphonothioates using metal-containing systems (e.g., 1) was achieved. The catalytic methanolysis of a SCH2CH2NEt 2 derivative, an analogue of the organophosphorus chemical warfare material VX, was predicted, and the catalyzed methanolysis of S-(3,5-dichlorophenyl) O-ethyl methylphosphonothioate was shown to involve a concerted displacement of the aryl thioate (transition state 2)
STEREOCHEMISTRY OF SOME REACTIONS BETWEEN ALKYL S-METHYL METHYLPHOSPHONOTHIOATES AND CHIRAL ALKOXIDES
Hall, C. Richard,Inch, Thomas D.,Pottage, Colin,Williams, Nancy E.
, p. 4909 - 4918 (2007/10/02)
With R-(+) ethyl (or methyl) S-methyl methylphosphonothioate and (+)-pinacolyl alkoxide competitive and highly stereoselective displacements of O-alkyl and S-methyl occur, both reactions being with inversion of configuration.With the enantiomeric S-(-) ethyl (and methyl) S-methyl methylphosphonothioates and (+)-pinacolyl alkoxide the reactions, although still competitive, are no longer stereoselective.In contrast similar reactions with the sodium salt of (-)-menthol, (which might be considered to be the mirror image of (+)-pinacolyl alkoxide) occur highly stereoselectively with the S-(-) but not with R-(+) enantiomers.The displacement of O-alkyl from alkyl S-methyl methylphosphonothioates by ethoxide, pinacolyl alkoxide and menthyl alkoxide is not observed when methoxide is the nucleophile; in this case only displacement of S-alkyl group occurs.