Synthesis of monoesters ofD-sorbitol and aromatic acids

Water-soluble monoesters ofD-sorbitol with aromatic acids have been synthesized by the transesterification of their methyl esters. The structures of the compounds obtained have been confirmed by IR, UV, and¹³C NMR spectroscopies.A. B. Bekturov Institute of Chemical Sciences, Academy of Sciences of the Republic of Kazakhstan, Almaty [Alma-Ata], ul. Sh. Ualikhanova, 106, fax 61 57 65. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 735–737, September–October, 1997.     

Synthesis and antiviral activity of adamantyl-containing phosphonous and phosphinic acids

The method of adamantly-containing phosphonous and phosphinic acids preparation, based on radical addition of hypophosphorous acid and sodium hypophosphite to unsaturated derivatives of adamantane, has been developed. Unsymmetrical phosphinic acids have been prepared by reacting bistrimetylsilyl esters of phosphonous acids with halides. The obtained phosphinic acids exhibit antiviral activity against herpes simplex virus, influenza A (H5N1), respiratory syncytial virus, and adenovirus.     

Solvent extraction studies using phosphonic acid monoesters

The extraction of radioactive⁶⁰Co by ethyl hydrogen benzoyl phosphonate (HEBOP) has been investigated. Different parameters that may effect this extraction such as the change in pH and [HEBOP] were studied. Extraction was carried out in three organic solvents. In addition, the equilibrium constants were determined at different temperatures and the thermodynamic parameters for such extraction process were calculated.     

Synthesis of bi-and tricyclic monoesters of dicarboxylic acids

A thermal addition of aliphatic dicarboxylic acids to bicyclo[2.2.1]-heptene hydrocarbons and to tricyclo[5.2.1.0^2,6]deca-3,8-diene was investigated and new samples of dicarboxylic acids alicyclic monoesters were synthesized. Some of monoesters synthesized have a pleasant fragrance and can find application as fragrance substances. They are also of interest as initial components for preparation of new organic compounds.     

Solvent extraction studies using phosphonic acid monoesters

The extraction of radioactive^152–154Eu by ethyl hydrogen benzyl phosphonate (HEBP) and ethyl hydrogen benzoyl phosphonate (HEBOP) in n-hexane from an aqueous solution of ionic strength 0.1M (Na⁺, HClO₄) has been investigated at different temperatures and the thermodynamic functions evaluated. HEBOP was found to be more efficient than HEBP as extractant. In addition, the stability constant of the extracted complexes were determined.     

Pd-catalyzed regio- and stereoselective cyclization-heck reaction of monoesters of 1,2-allenyl phosphonic acids with alkenes

[reaction: see text] The cyclization-Heck reactions of monoesters of 1, 2-allenyl phosphonic acids with alkenes were studied. The reaction afforded 4-(1-Z-alkenyl)-2-ethoxy-2,5-dihydro[1,2]oxaphosphole 2-oxides regio- and stereoselectively. Pd(II) was regenerated from the in situ formed Pd(0) using CaH2(cat.)/NaI/O2 or benzoquinone to furnish the catalytic cycle.     

Mild Arbuzov reactions of phosphonous acids

A very mild and simple method for the preparation of phosphinic acids from phosphonous acids through the intermediacy of silylalkyl phosphonites is described.     

Acid chlorides of unsaturated phosphonous acids

Summary The dichloride of -ethoxyvinyl-, -isooctyloxyvinyl-, and 2-chloro-3-methylbut-3-enylphosphonous acids have been synthesized and characterized for the first time. The diethyl ester of -ethoxyvinylphosphonous acid has been-obtained from the dichloride of -ethoxyvinylphosphonous acid.     

Halodephosphorylation of α,β-unsaturated phosphonic acid monoesters

Reaction of α,β-ethylenic and acetylenic phosphonic acid monoesters with (biscollidine)iodine(I) or (biscollidine)bromine(I) hexafluorophosphate led to α,β-unsaturated halides by, without precedent, dephosphorylation reactions.     

Synthesis and coordination chemistry of fluorinated phosphonic acids

Phosphonic acids [(HO)₂P(O)C₂H₄C_nF_2n+1] (n = 4, 6) and [(HO)₂P(O)C₆H₄-4-C_nF_2n+1] (n = 0, 1, 6) have been prepared in good yields. Deprotonation and reaction with cis-[PtCl₂(PPh₃)₂] affords fluorinated platinum complexes which have been characterised by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structures of [Pt{O₂P(O)C₆H₄-4-F}(PPh₃)₂], [Pt{O₂P(O)C₆H₄-4-CF₃}(PPh₃)₂] and [Pt{O₂P(O)C₂H₄C₆F₁₃}(PPh₃)₂] have been determined by single crystal X-ray diffraction.     

Synthesis methods of (1-aminocyclopropyl)phosphonic acids

Known methods of preparation of (1-aminocyclopropyl)phosphonic acids and their derivatives are analyzed.     

Synthesis of phosphinic and phosphonic analogs of aromatic amino acids

The reaction of aryl and aralkyl aldoximes with hypophosphorous acid resulted in aminophosphinic acids, which were oxidized into the corresponding aminophosphonic acids. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–140, January, 1997.     

Synthesis of bis(aryloxymethyl)phosphonic acids and their esters

Conclusions Synthetic methods were developed and bis(aryloxymethyl)phosphonic acids and their esters were synthesized.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 951–953, April, 1969.     

Synthesis and stability study of dental monomers containing methacrylamidoethyl phosphonic acids

Three new dental monomers containing methacrylamidoethyl phosphonic acids were synthesized. The structures of the synthesized monomers were determined with electrospray mass spectrometry (ESMS), Fourier transform infrared, and NMR. The hydrolytic stabilities of the synthesized monomers and a commercial monomer, 2‐methacryloyloxyethyl phosphoric acid (MEP; used as a control), were studied with flow injection (FI)/ESMS, ¹H NMR, and ³¹P NMR analysis of a CD₃OD/D₂O (4:1 v/v) solution of each monomer before and after storage at 60 °C for 2 months. The ¹H NMR and ³¹P NMR chemical shifts of the monomers 2‐methacrylamidoethylphosphonic acid ( I ) and N,N′‐[4,4′‐(propane‐2,2‐diyl)‐bis(phenoxy‐2‐hydroxypropyl)]‐bis(2‐methacrylamidoethylphosphonic acid) ( II ) showed little change after storage at 60 °C for 2 months, but those of MEP changed significantly. FI/ESMS also showed that MEP was nearly completely decomposed, whereas monomers I and II remained largely intact. MEP could react with H₂ZrF₆ to form ternary zirconium fluoride complexes that were partially soluble in methanol, but all the monomers containing phosphonic acids formed precipitates. This study demonstrates that ESMS is a more sensitive and effective method than NMR for studying the hydrolytic stability or degradation of dental monomers. The new monomers containing methacrylamidoethyl phosphonic acids have higher hydrolytic stability than methacrylate phosphate monomers and may be used in dental bonding agents and other dental materials. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 99–110, 2007