107811-56-3Relevant academic research and scientific papers
Synthesis and coordination properties of tripodal ligand on the triphenylphosphine oxide platform with carbamoyl side arms
Kudryavtsev, Igor Yu.,Baulina, Tatyana V.,Pasechnik, Margarita P.,Matveev, Sergei V.,Matveeva, Anna G.
, p. 946 - 962 (2014)
A new tripodal O-donor ligand, tris(2-N,N-dibutylcarbamoylmethoxyphenyl)phosphine oxide (L), was synthesized. This potentially tetradentate ligand L exhibits variable denticity upon complexation with UO2(NO3)2, Nd(NO3
Coordination and extraction of lanthanides(III) with tripodal ligands on the triphenylphosphine oxide platform: Effect of uncoordinating substituents
Matveeva, Anna G.,Kudryavtsev, Igor Yu.,Pasechnik, Margarita P.,Vologzhanina, Anna V.,Baulina, Tatyana V.,Vavina, Anna V.,Sukat, Georgiy Ya.,Matveev, Sergey V.,Godovikov, Ivan A.,Turanov, Alexander N.,Karandashev, Vasilii K.,Brel, Valery K.
, p. 71 - 82 (2018)
A ligand system containing three carbamoyl moieties secured onto a triphenylphosphine oxide platform (2-R2NC(O)CH2OC6H4)3PO, where R = Me (1), Bu (2), and cyclo-Hex (3) has been developed for lanthanide complexation and extraction from aqueous solutions. The influence of non-coordinating alkyl substituents at the nitrogen atoms in the carbamoyl side arms on coordination and extraction properties of tripodal ligands 1–3 was studied. Two new ligands 1 and 3 with alkyl substituents of different bulkiness were synthesized and characterized by spectroscopic methods. Single-crystal X-ray structures have been determined for ligands 1 and 2. The selected coordination chemistry of ligands 1–3 with Ln(NO3)3 (Ln = La, Nd, Lu) has been evaluated. The 1:1 complexes of all ligands 1–3 were synthesized and characterized via elemental analysis and IR spectroscopy; in addition, the crystal structure of the ligand 1 complex with neodymium nitrate was determined by X-ray diffraction. Solution structure of 1:1 complexes was examined by IR and multinuclear (1H, 13C, and 31P) NMR spectroscopy. A formation of 1:2 complexes with lanthanum and lutetium nitrates (IR, NMR, ESI-MS) has been examined and structure of the major components of 1:2 complexes solutions has been suggested for ligands 1–3. Preliminary extraction studies of Ln(III) (Ln = La, Nd, Eu, Lu) from 3 M NH4NO3 into 1,2-dichloroethane show that ligands 2 and 3 recover lanthanides much better than their mono analog [2-(Bu2NC(O)CH2O)-5-Et-C6H3]P(O)Ph2 and known extractant Ph2P(O)CH2C(O)NBu2.
Synthesis, Molecular, and Crystal Structure of Tris(2-carbamoylmethoxyphenyl)phosphine Oxide
Artem’ev, A. V.,Bagryanskaya, I. Yu.,Baulina, T. V.,Brel, V. K.,Kudryavtsev, I. Yu.,Pasechnik, M. P.
, p. 1840 - 1844 (2020)
Abstract: New tripodal ligand, tris(2-carbamoylmethoxyphenyl)phosphine oxide, has been synthesized via the alkylation of tris(2-hydroxyphenyl)phosphine oxide with chloroacetamide. The ligand structure has been studied by means of IR and NMR (1H
New tripodal ligand on the triphenylphosphine oxide platform with 1,2,3-triazole side arms: synthesis, structure, coordination, and extraction properties
Kudryavtsev, Igor Y.,Bykhovskaya, Olga V.,Matveeva, Anna G.,Baulina, Tatyana V.,Pasechnik, Margarita P.,Matveev, Sergey V.,Vologzhanina, Anna V.,Turanov, Alexander N.,Karandashev, Vasilii K.,Brel, Valery K.
, p. 1705 - 1713 (2020)
Abstract: New hybrid tripodal propeller ligands on the triphenylphosphine oxide platform with triazole rings in the side arms and alkyl and aryl substituents in the triazole fragments have been synthesized by the click reaction. Composition and structure of the prepared compounds have been established by vibrational (IR, Raman) and multinuclear (1H, 13C, 31P) NMR spectroscopy, elemental analysis, and mass spectrometry. Coordination and extraction properties of the prepared compounds toward Pd(II) have been studied by the example of one of the ligands. Graphic abstract: [Figure not available: see fulltext.]
A reactivity study of phenyl and ferrocenyl phosphates within the anionic phospho-Fries rearrangement
Korb, Marcus,Lang, Heinrich
, p. 30 - 32 (2016/08/11)
Temperature-dependent anionic phospho-Fries rearrangements of ferrocenyl/phenyl phosphates P(O)(OFc)n(OPh)3???n (Fc?=?Fe(η5-C5H5)(η5-C5H4); n?=?0,1,2,3) were investigated. Whereas ferrocenyls solely undergo one rearrangement per reaction step, the number of phenyl-based 1,3-O?→?C shifts depends on the temperature. This results in different types of otherwise hardly accessible mixed ferrocenyl/phenyl organophosphorus compounds. Detailed investigations of the triple-rearrangement of triphenyl phosphate (n?=?0) reveals a consecutive formation of its phosphonate and phosphinate prior to the known phosphane oxide.
Synthesis and coordination properties of new preorganized ligand on the triphenylphosphine oxide platform
Kudryavtsev,Baulina,Pasechnik,Aisin,Matveev,Petrovskii,Nifant'Ev
, p. 1086 - 1090 (2014/03/21)
Tris(2-cyanomethoxyphenyl)phosphine oxide was synthesized by the reaction of tris-(2-hydroxyphenyl)phosphine oxide with chloroacetonitrile. Its coordination properties were studied for the complexation with neodymium(III) and copper(ii) nitrates using vibrational spectroscopy, NMR, and quantum chemical calculations.
Synthesis of a family of triarylphosphanes with fluorous phase affinity
Sinou, Denis,Maillard, David,Pozzi, Gianluca
, p. 269 - 275 (2007/10/03)
A very efficient synthesis of new perfluoro-functionalized triarylphosphanes using an oxygen substituent as the branching point for the introduction of the perfluoro chain has been developed. This approach enabled the introduction of the perfluoro tail at the para, meta, and oitho position, giving highly perfluorinated analogues of triphenylphosphane con-taining between 54 and 59 wt% fluorine. This methodology has been extended to the synthesis of a perfluoro analogue of l,2-bis(diphenylphosphanyl)ethane. Fluorous/organic partition coefficients of some of the perfluorophosphanes have been measured, as well as their rates of oxidation. WILEY-VCH Verlag GmbH, 2002.
Bridging the final gap in stereocontrolled Wittig reactions: Methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity
Wang, Qian,El Khoury, Mirella,Schlosser, Manfred
, p. 420 - 426 (2007/10/03)
After treatment with an appropriate base (butyllithium or sodium amide), 2-alkenyltris(2-methoxymethoxyphenyl)phosphonium salts carrying an allyl, crotyl, or prenyl (3-methyl-2-butenyl) side chain condense with saturated or unsaturated aldehydes to give conjugated dienes with Z/E ratios ranging from 90:10 to >99:1 and averaging 96:4. Owing to steric congestion, yields are only moderate (on average 41%; extremes 10-79%). The nonvolatile tris(2- methoxymethoxyphenyl)phosphine oxide by-product can be readily isolated and reduced to recover the phosphane starting material, or it may be hydrolyzed to the water-soluble tris(2-hydroxyphenyl)phosphine oxide.
METALLATION INDUCED REARRANGEMENT OF TRIARYLPHOSPHATES TO TRIS (2-HYDROXYARYL) PHOSPHINE OXIDES
Dhawan, Barlam,Redmore, Derek
, p. 465 - 468 (2007/10/02)
A novel one step conversion of traryl phosphates to tris (2-hydroxyaryl) phosphine oxides involving a metallation induced triple migration of phosphorus from O --> C is reported.
