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
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
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
