54100-47-9Relevant academic research and scientific papers
T -Butylphenyl-(1-Naphthyl)Phosphinothioic Acids and Their Selenium Analogs: Synthesis of the Racemic Mixtures and Attempts to Isolate the Enantiomers of t -Butyl-1-Naphthylphosphinothioic Acid
Pokora-Sobczak, Patrycja,Mielniczak, Grazyna,Krasowska, Dorota,Chrzanowski, Jacek,Zaj?c, Adrian,Drabowicz, Józef
, p. 694 - 699 (2015)
Synthesis of racemic t-butyl-1-naphthylphosphinothio(seleno)ic acids and attempts to isolate the enantiomers of t-butyl-1-naphthylphosphinothioic acid are described.
Chiral t-butylphenylphosphinothioic acid: A useful chiral solvating agent for direct determination of enantiomeric purity of alcohols, thiols, amines, diols, aminoalcohols and related compounds
Omelanczuk, Jan,Mikolajczyk, Marian
, p. 2687 - 2694 (1996)
Enantiomers of t-butylphenylphosphinothioic acid were found to be useful chiral solvating agents (CSAs) for 1H-NMR determination of enantiomeric excess (ee) of many classes of chiral organic compounds, such as alcohols, diols, thiols, mercaptoalcohols, amines, aminoalcohols, hydroxyacids and related compounds.
A new procedure for the synthesis of optically active t-butylphenylphosphinothioic acid
Drabowicz, Jzef,Pokora-Sobczak, Patrycja,Zajc, Adrian,Wach-Panfilow, Paulina
, p. 674 - 677 (2015/02/19)
A new procedure for the synthesis of optically active t-butylophenylphosphinothioic acid as an enantiomerically pure dextrorotatory enantiomer having the absolute configuration (R), by a reaction of the racemate of secondary t-butylphenylphosphine oxide with elemental sulfur in the presence of a molar equivalent of the levorotatory enantiomer of enantiomerically pure (S)-α-phenylethylamine, is reported. It is obvious that with the use of the dextrorotatory enantiomer of α-phenylethylamine, the levorotatory enantiomer of this thioacid will be isolated.
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
experimental part, 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
Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions
Haynes, Richard K.,Au-Yeung, Tin-Lok,Chan, Wai-Kuen,Lam, Wai-Lun,Li, Zhi-Yi,Yeung, Lam-Lung,Chan, Albert S. C.,Li, Pauline,Koen, Mark,Mitchell, Craig R.,Vonwiller, Simone C.
, p. 3205 - 3216 (2007/10/03)
P-Chiral tertiary phosphane oxides have been prepared from each of the secondary phosphane oxides racemic 1, (S(p))-(-)-4 and (Rp)-(+)-tert-butylphenylphosphane oxide (5) by lithiation with LDA or nBuLi, or sodiation with sodium hydride, in THF, and then by treatment with a series of primary alkyl halides. Doubly P-chiral ditertiary bis(phosphane oxides) are also obtained from these metallated secondary phosphane oxides by treatment with electrophiles based on straight-chain, tartrate-derived, and bishalomethylarene dihalides. In general, the bis-phosphane oxides are obtained in good yields. However, when the α,ω-dihalide bears an embedded heteroatom (O or Si), yields are diminished. The enantiomeric purity of each of the products was assessed through admixture with (R(p))- and (S(p))-tert-butyl(phenyl)phosphanylthioic acids and measurement of the tert-butyl resonances in the 1H-NMR spectra. In all cases, the act of metallation of the enantiomerically pure secondary phosphane oxide followed by its alkylation is not accompanied by detectable racemization. This method for preparing P-chiral tertiary phosphane oxides is therefore more straightforward than those described previously.
Srereoselective Synthesis and Stereochemistry of Optically Active tert-Butylphenylphosphine Sulfide
Skrzypczynski, Zbigniew,Michalski, Jan
, p. 4549 - 4551 (2007/10/02)
Stereoselective reduction of the mixed anhydride of tert-butylphenylphosphinothioic acid trifluoromethanesulfonic acid by sodium borohydride provides optically active tert-butylphenylphosphine sulfide of high optical purity.A synthesis of optically active
