3732-85-2Relevant academic research and scientific papers
Enantiopure cyclic O-substituted phenylphosphonothioic acid: Synthesis and chirality-recognition ability
Ribeiro, Nigel,Kobayashi, Yuka,Maeda, Jin,Saigo, Kazuhiko
experimental part, p. 438 - 448 (2012/01/02)
As a new acidic selector (resolving agent), we synthesized an enantiopure O-alkyl phenylphosphonothioic acid with a seven-membered ring ((R)-5), which was designed on the basis of the results for the enantioseparation of 1-arylethylamine derivatives with acyclic O-ethyl phenylphosphonothioic acid (I). The phosphonothioic acid (R)-5 showed unique chirality-recognition ability in the enantioseparation of 1-naphthylethylamine derivatives, aliphatic secondary amines, and amino alcohols; the ability was complementary to that of I. The X-ray crystallographic analyses of the less- and more-soluble diastereomeric salts showed that hydrogen-bonding networks in the salt crystals are 21-column-type with a single exception which is cluster-type. In the cases of the 21-column-type crystals, stability of the crystals is firstly governed by hydrogen bonds to form a 21-column and secondly determined by intra-columnar T-shaped CH/π interaction(s), intra-columnar hydrogen bond(s), inter-columnar van der Waals interaction and/or inter-columnar T-shaped CH/π interaction(s). In contrast, the cluster-type salt crystal is stabilized by the assistance of inter-cluster T-shaped CH/π and van der Waals interactions. To realize still more numbers of intra- and inter-columnar and -cluster T-shaped CH/π interactions, the seven-membered ring of (R)-5 plays a considerable role. Copyright
Nucleophilic Substitution in Benzylic Thiophosphinyl and Thiophosphonyl Chlorides: the Contribution of Elimination-Addition Pathways with Methylenethiooxophosphorane (Thiophosphene) Intermediates
Coogan, Michael P.,Harger, Martin J. P.
, p. 2101 - 2108 (2007/10/02)
For the reactions of ArCH2P(S)(Ph)Cl and ArCH2P(S)(NMe2)Cl with Et2NH, changing ArCH2 from benzyl to 4-nitrobenzyl increases the rates of substitution by factors of 80 and >103, respectively, and reduces markedly the ability to discriminate bet
The ortho Matallation of N,N,N',N'-Tetramethyl-P-phenyl-phosphonothioic Diamide
Craig, Donald C.,Roberts, Nicholas K.,Tanswell, Janine L.
, p. 1487 - 1496 (2007/10/02)
The reaction of C6H5P(S)(NMe2)2 (2) with BuLi in diethyl ether/hexane mixture gives the ortho-metallated species o-LiC6H4P(S)(NMe2)2 (3), which has been characterized by 31P and 13C n.m.r. spectroscopy, and by preparation of the derivatives Ro-C6H4P(S)(N
Evidence for a Methylenethioxophosphorane (Thiophosphene) Intermediate in Nucleophilic Substitution at a Benzylthiophosphonyl Centre
Coogan, Michael P.,Harger, Martin J. P.
, p. 1745 - 1746 (2007/10/02)
The remarkably high rate of the reaction of p-NO2C6H4CH2P(S)(NMe2)Cl with Et2NH, the presence of deuterium in the benzylic methylene group of the product formed with Et2ND, and the relative lack of discrimination between competing Me2NH and Et2NH, suggest
