Patrycja Pokora-Sobczak

Optically Active T-Butylphenylphosphinothioic Acid: Synthesis, Selected Structural Studies and Applications as a Chiral Solvating Agent

Abstract Synthesis, structural studies and the use of the (−)-(S)- and (+)-(R) enantiomers of t-butylphenylphosphinothioic acid as a chiral solvating agent for the determination of enantiomeric purity is discussed. Systems that are the most extensively studied are emphasized. GRAPHICAL ABSTRACT

Phenol-Derived Chiral Auxiliaries as Substrates in the Synthesis of Optically Active Phosphonic Acid Derivatives: Synthetic and Structural Aspects

GRAPHICAL ABSTRACT Abstract Preparation of chiral phosphonic acid amidoesters or diesters derived from diastereomerically pure 1-[α-N-1-phenylethylamino]benzyl-2-naphthol or 2,2′-dihydroxy-1,1′-binaphthyl are reported. The attempted ring opening reactions of the isolated compounds with a few nucleophiles are also discussed. Basic structural data for phenyl amidophosphonate and phenylamidothiophosphonate derived from diastereomerically pure 1-[α-N-1-phenylethylamino]benzyl-2-naphthol based on X-ray structural analysis are also presented.

A stereogenic heteroatom-containing substituent as an inducer of chirality in the derivatives of thiophenes (mono, oligo, and poly), fullerenes C60, and multiwalled nanotubes

GRAPHICAL ABSTRACT Abstract Synthetic procedures applied recently in our laboratory for the preparation of a new thiophene, fullerene C60 and multiwalled carbon nanotube (MWCNT) derivatives functionalized with a substituent containing an achiral and/or a stereogenic heteroatom are reviewed. Polymerization reactions of selected optically active 2-(3′-thienyl)ethyl aryl(alkyl) sulfoxides and tert-butyl-[2-(3′-thienyl)ethyl]phenylphosphine oxide are also mentioned. Mechanistic and stereochemical aspects of the presented protocols are discussed.

Carbon nanotubes functionalized with sulfur, selenium, or phosphorus or substituents containing these elements

GRAPHICAL ABSTRACT ABSTRACT The preparation of multiwalled carbon nanotubes (MWCNTs) and singlewalled carbon nanotubes (SWCNTs) doped with sulfur, selenium, or phosphorus atom or functionalized with substituents containing these elements (including a stereogenic heteroatom) is presented in this mini-review. Structural studies of newly isolated derivatives based on suitably selected spectroscopic techniques are also discussed briefly. Chances for applications of obtained carbon nanotubes doped with these heteroatoms or functionalized with substituents containing these heteroatoms are also mentioned.

High-performance liquid chromatographic enantioseparation of N-aryl-thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide-based chiral stationary phases

The first successful enantioseparation of representative O,O-diphenyl-N-arylthioureidoalkylphosphonates, (±)-Ptc-ValP (OPh)2 & (±)-Ptc-LeuP (OPh)2 and thiourylenedi(isobutyl phosphonate), Tcm[ValP (OPh)2 ]2 on analytical and semipreparative scale was achieved by high-performance liquid chromatography using polysaccharide-based chiral stationary phases (CPs). Atc-AAP (OPh)2 was obtained using modified tricomponent condensations of the corresponding aldehydes, N-arylthiourea and triphenyl phosphite whereas Tcm[ValP (OPh)2 ]2 by the condensations of aldehydes, thiourea, and triphenyl phosphite. The prepared, racemic (±)-Atc-AAP (OPh)2 [(±)-Ptc-ValP (OPh)2 , (±)-Ptc-LeuP (OPh)2 , (±)-Ptc-PglyP (OPh)2 and (±)-Ntc-PglyP (OPh)2 ] and racemic (±)-Tcm[AAP (OPh)2 ]2 [(±)-Tcm[NvaP (OPh)2 ]2 & (±)-Tcm[ValP (OPh)2 ]2 ] were adequately characterized and used for chromatographic separations on high-performance liquid chromatography-chiral stationary phases. The best results were obtained for (±)-Ptc-ValP (OPh)2 , (±)-Ptc-LeuP (OPh)2 and (±)-Tcm[ValP (OPh)2 ]2 .

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

GRAPHICAL ABSTRACT Abstract Synthesis of racemic t-butyl-1-naphthylphosphinothio(seleno)ic acids and attempts to isolate the enantiomers of t-butyl-1-naphthylphosphinothioic acid are described.