3577-87-5Relevant academic research and scientific papers
Aerobic photooxidation of phosphite esters using diorganotelluride catalysts
Oba, Makoto,Okada, Yasunori,Nishiyama, Kozaburo,Ando, Wataru
supporting information; experimental part, p. 1879 - 1881 (2009/10/10)
Diorganotellurides containing bulky aromatic substituents are found to catalyze the photooxidation of phosphite esters using aerobic oxygen as a terminal oxidant. A Hammett plot with substituted triaryl phosphites yielding p = 2.88 agrees with a nucleophilic oxygen transfer from telluroxide to phosphite.2009 American Chemical Society.
Horner olefination reaction in organic sulfur chemistry and synthesis of natural and bioactive products
Mikolajczyk, Marian,Midura, Wanda H.,Mohamed Ewas, Ashraf M.,Perlikowska, Wieslawa,Mikina, MacIej,Jankowiak, Aleksandra
scheme or table, p. 313 - 325 (2009/04/06)
This article outlines the results of our work on the application of the Horner olefination reaction for the synthesis of unsaturated sulfur compounds. A general synthesis of racemic and optically-active α,β-unsaturated sulfoxides by the Horner reaction with α-sulfinylmethylphosphonates as olefination reagents is presented. We demonstrated how the structure of the phosphonate moiety may control the E- and Z-stereoselectivity in the above reaction. The use of racemic and optically-active α- sulfinylvinylphosphonates in tandem Michael addition/Horner olefination reaction leads to a wide range of carbocyclic and heterocyclic vinyl sulfoxides. In second part of this account a new strategy for the synthesis of functionalized cyclopentenones is briefly described. The synthesis and reactivity of 3-phosphorylmethyl-cyclopentenones is discussed as a platform for developing the synthesis of racemic rosaprostol, enantiomeric prostaglandin B1 methyl esters, enantiopure isoterreins, natural and unnatural neplanocin A and enantiomeric forms of phytoprostane B1 type I. Copyright Taylor & Francis Group, LLC.
Bisphosphonate prodrugs. Synthesis and identification of (1-hydroxyethylidene)-1,1-bisphosphonic acid tetraesters by mass spectrometry, NMR spectroscopy and x-ray crystallography
Turhanen, Petri A.,Ahlgren, Markku J.,Jaervinen, Tomi,Vepsaelaeinen, Jouko J.
, p. 115 - 133 (2007/10/03)
The preparation and identification of symmetric, H3CC(OH)[P(O)(OR)2]2, where R=Me, Et, Pr1, Ph, and non-symmetric, H3CC(OH)[P(O)(OR1)(OR2)][P(O)(OR3)(O R4)], where R1=Me, R2=R3=R4=Ph; R1=R2=R3=Ph, R4=Me; R1=R3=Me, R2=R4=Ph; R1=R2=Et, Pr1, Ph and R3=R4=Me: tetraester derivatives of etidronate have been studied. Compounds were prepared from HP(O)(OR1)(OR2) and AcP(O)(OR3)(OR4) species under reflux. Mechanism studies have been made using HP(O)(OCD3)(OPh) and AcP(O)(OMe)(OPh) as starting materials. 1H, 13C, 31P NMR data and the MS fragmentation data in the gas phase are reported. The solid-state structures are given for three of the compounds, where R=Et, Ph and R1=R2=Ph, R3=R4=Me.
Synthesis of Phosphonates: a Modified Arbuzov Procedure
Wang, Meng Fang,Crilley, Martine M. L.,Golding, Bernard T.,McInally, Tom,Robinson, David H.,Tinker, Alan
, p. 667 - 668 (2007/10/02)
Reactions of 6-iodogalactosides with either methyl or isopropyl diphenyl phosphite lead to diphenylphosphoryl derivatives; these can be converted by ester exchange into dibenzylphosphoryl derivatives, which are convenient precursors of carbohydrate phosphonic acids.
SYNTHESIS OF AN UNREACTIVE YLID DESIGNED AS A -C-P-C-P DIPHOSPHATE ISOSTERE SYNTHON
McClard, Ronald W.,Jackson, Steven A.
, p. 27 - 32 (2007/10/02)
The complex phosphonium salt 3 was synthesized from bis(hydroxymethyl)phosphinic acid in five steps.The ylid, 2a, produced in situ from 3a, did not react as expected with aldehydes to give the desired phosphonylphosphinyl derivative.Since 2a is actually more basic than the homologous 1, the observed lack of reactivity is apparently not a result of electronic factors.Key words: Analog; diphosphate; phosphinate; phosphonate; phosphonium salt; ylid.
α-PHOSPHORYL SULFOXIDES. V. SYNTHESIS AND CRYSTAL AND MOLECULAR STRUCTURE OF O,O-DIPHENYLPHOSPHORYLMETHYL PHENYL SULFOXIDE
Mikolajczyk, Marian,Midura, Wanda,Wieczorek, Michal W.,Bujacz, Grzegorz
, p. 19 - 26 (2007/10/02)
The crystal structure of the title compound (1) was determined by X-ray diffraction technique from diffractometer intensity measurements; C19H17O4PS, triclinic space group P1, a=9.4630(6), b=9.8814(6), c=10.2977(5) Angstroem, α=84.37(4), β=84.59(5), γ=70.40(4) deg, 2998 reflections, R=0.0402.The molecule of 1 adopts a conformation in which the diphenoxyphosphoryl and phenyl groups are in antiperiplanar orientation around the sulfur-methylene carbon bond.
Successive Displacements of Phenoxy by Methoxy Groups in Triphenyl Phosphite Ozonide: Mechanism of the Accelerated Singlet Oxygen Formation with Pyridine and Methanol
Bartlett, Paul D.,Lonzetta, Charles M.
, p. 1984 - 1988 (2007/10/02)
The ozonides from triphenyl phosphite, methyl diphenyl phosphite, and phenyl dimethyl phosphite form a series (1-3) which liberate singlet thermally at rates incresing by an order of magnitude for each substitution of methoxy for phenoxy.Trimethyl phosphite ozonide (4) fits in this series, although the very low temperature limit of its stability has not been determined.When triphenyl phosphite ozonide (1) is treated with methanol and pyridine in methylene chloride and yields singlet oxygen at an accelerated rate, the phenyl methyl phosphates 6 and 7 and trimethyl phosphate (8) are produced in a total amount corresponding to the singlet oxygen evolved.The lower the temperature, the greater the predominance of trimethyl phosphate (8) in the product.Each of the mixed phosphite ozonides 2 and 3 is in turn subject to accelerated singlet oxygen formation by the action of methanol and pyridine; in each case the phosphates formed contain at least one more methoxy group than the starting ozonide.These facts establish the mechanism of the accelerated singlet oxygen liberation as a successive displacement of phenoxy by methoxy groups on the initial phosphite ozonide, each newly formed aliphatic-aromatic phosphite ozonide decomposing thermally at its own increased rate.
