55705-77-6Relevant 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 (2016/01/15)
Synthesis of racemic t-butyl-1-naphthylphosphinothio(seleno)ic acids and attempts to isolate the enantiomers of t-butyl-1-naphthylphosphinothioic acid are described.
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.
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.
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 (2007/10/03)
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.
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
OPTICALLY ACTIVE TRIORGANOSILYL ESTERS OF PHOSPHORUS. SYNTHESIS AND STRUCTURE
Chojnowski, J.,Cypryk, M.,Michalski, J.,Wozniak, L.,Corriu, R.,Lanneau, G.
, p. 385 - 398 (2007/10/02)
We report this synthesis of the first optically active silyl esters of phosphorus having two centres of chirality : one on silicon and the other on phosphorus.Compounds are obtained of general formula : t-BuPhP(X)YSiαNpPhMe X,Y=O, O(1); S, O(2); Se, O(3); S, S(4); doublet, O(5) including 1 and 3 with optical activity located on Si, 2 and 5 with the activity on Si or P and on both these centres, 4 only racemic.Absolute configurations are determined. 31P and 29Si NMR spectra of these models and their trimethylsilyl analogues are reported.The triorganosilyl group is always preferentially bound to phosphorus through oxygen atom.Surprisingly, diastereotopic NMR chemical shifts exclude the fast 1,3 migration in esters 1 and 4. 29Si NMR spectra correspond to a tetracoordinate silicon atom.
