77314-08-0Relevant academic research and scientific papers
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.
, 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
Use of Carbohydrate Derivatives for Studies of Phosphorus Stereochemistry. Part 8. Preparation and Some Reactions of 1,3,2-Oxazaphospholidine-2-ones and -2-thiones derived from 2-Deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucopyranose
Hall, C. Richard,Inch, Thomas D.,Pottage, Colin,Williams, Nancy E.,Campbell, Malcolm M.,Kerr, Patrick F.
, p. 1967 - 1975 (2007/10/02)
The four cyclic phosphorus esters from the reaction of MePSCl2 with 2-deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucopyranose (1) have been separated with difficulty, and structures assigned.Ring-opening of the isomers and subsequent detachment of the chir
Stereochemistry and Reactions of Aziridinylphosphinothionates Derived from Amino Acids
Hirashima, Akinori,Eto, Morifusa
, p. 829 - 838 (2007/10/02)
Aziridinylphosphinothionates were prepared from optically active ethyl hydrogen phenylphosphonothionates and 1-bromo-2-alkanamines derived from leucine or valine.The aziridine ring was opened by the action of some nucleophiles.Refluxing the aziridinylphosphinethionates in acetone with sodium iodide caused hydrolysis accompanied by the rearrangement of the sulfur atom to give β-mercaptoethylphosphonamidates.The reaction mechanism was discussed eith stereochemical considerations.The insecticidal activity of the products was also examined.
STEREOCHEMISTRY OF THE BASE-CATALYZED METHANOLYSIS OF 2-PHENYL-TETRAHYDROPYRROLO-1,3,2-OXAZAPHOSPHOLES
Koizumi, Toru,Yanada, Reiko,Takagi, Hiroyasu,Hirai, Hajime,Yoshii, Eiichi
, p. 477 - 480 (2007/10/02)
Diastereomerically pure bicyclic oxazaphospholes were prepared from L-prolinol and phenylphosphonic or thiophosphonic dichloride and their absolute configurations were determined based on the interpretation of NMR spectra.The base-catalyzed methanolysis o
1,3,2-Thiazaphospholidin-2-ones Derived From Ephedrine. Preparation and Stereochemistry of Ring-opening Reactions
Hall, C. Richard,Williams, Nancy E.
, p. 2746 - 2750 (2007/10/02)
1,3,2-thiazaphospholidin-2-ones are prepared by rearrangement of the corresponding 1,3,2-oxazaphospholidine-2-thiones.In both the phosphono- and phosphoro-series treatment with alkoxide results in P-N bond cleavage with inversion of configuration, while treatment with Grignard reagents results in P-S bond cleavage with retention of configuration.The products are consistent with a mechanism which involves initial nucleophilic attack opposite endocyclic nitrogen.
CHIRAL PHENYLPHOSPHONIC ESTERS, THEIR PREPARATION VIA ETHYL N- L-PROLINATE AND THEIR ABSOLUTE CONFIGURATIONS
Koizumi, Toru,Takagi, Hiroyasu,Yoshii, Eiichi
, p. 1403 - 1406 (2007/10/02)
Diastereomerically pure ethyl N--L-prolinate was prepared.From this intermediate various optically active phenylphosphonic acid derivatives have been obtained in high optical yields.Their absolute configurations have been det
