16934-93-3Relevant academic research and scientific papers
Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic Substitution at Phosphorus Center
Strzelecka, Dorota,Baok, Olga,Borowski, Piotr,Stankevi?, Marek
, p. 4922 - 4932 (2018/12/14)
Reaction of racemic phosphinic acid derivatives with chiral alcohols proceeds with predominant formation of one diastereomer. The highest level of enrichment has been obtained for transesterfication of racemic methyl benzylphenylphosphinate (64% de). The
Stereospecific halogenation of P(O)-H bonds with copper(II) chloride affording optically active Z1Z2P(O)Cl
Zhou, Yongbo,Wang, Gang,Saga, Yuta,Shen, Ruwei,Goto, Midori,Zhao, Yufen,Han, Li-Biao
supporting information; experimental part, p. 7924 - 7927 (2011/02/23)
A general and efficient method for the preparation of optically active Z1Z2P(O)Cl from the easily prepared optically active H-phosphinates and H-phosphine oxides was reported. H-Phosphinates and H-phosphine oxides react stereospecifi
Studies on the efficient generation of phosphorus-carbon bonds via a rearrangement of PIII esters catalysed by trimethylhalosilanes
Dabkowski, Wojciech,Ozarek, Alfred,Olejniczak, Sebastian,Cypryk, Marek,Chojnowski, Julian,Michalski, Jan
experimental part, p. 1747 - 1756 (2009/09/25)
Halotrimethylsilanes Me3SiX (X = Br, I) catalyse rearrangements of tricoordinate phosphorus esters R′R″P-OR into the corresponding phosphoryl systems R′R″P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by 31P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno PIII structures R′R″PX and silyl ethers ROSiMe3 and that they subsequently react to give the corresponding phosphorus silyl esters - Me 3SiOPR′R″-and alkyl halides RX. At higher temperatures these intermediates then react to form R′R″P(P)R compounds. This paper also features the surprising observation that when esters Ph 2POR and halotrimethylsilanes Me3SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph2R2P+X - and trimethylsilyl diphenylphosphinate - Ph2P(O) OSiMe3 - are formed as the major products. Experimental evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me3SiCl is not reactive and this paper explains why.
Stereospecific nucleophilic substitution of optically pure H-phosphinates: A general way for the preparation of chiral P-stereogenic phosphine oxides
Xu, Qing,Zhao, Chang-Qiu,Han, Li-Biao
body text, p. 12648 - 12655 (2009/05/09)
Contrary to the generally held view, it is found that the rapid epimerization of (-)-menthyl (RP)-phenylphosphinate under basic conditions is not due to the so far believed inherent stereolability of its corresponding anion but due to a reactio
New Methods for Probing the Chirality of 18O-Labelled Phospinic Acids
Kay, Paul B.,Trippett, Stuart
, p. 1813 - 1816 (2007/10/02)
The chirality of singly 18O-labelled methyl(phenyl)phosphinic acid can be probed by conversion into the diastereomeric myrtenyl esters by the action of myrtenyl bromide on the potassium salt of the acid in Me2SO in the presence of 18-crown-6.The Mitsunobu
Stereochemistry of Hydrolysis at an Acyclic Phosphoryl Centre leading to an Achiral Phosphorus Acid
Trippett, Stuart,White, Colin L.
, p. 251 - 252 (2007/10/02)
Alkaline hydrolysis of SP-methyl methylphenylphosphinate in 60percent H218O has been shown to involve predominant (>90percent) inversion of configuration at phosphorus; esterification of the resulting acid with the diazocompounds (2)
