Hydrolyse des sels de phospholium monomères: Préparation et propriétés des oxydes de 1,3-diénylphosphines

Mathey, François; Muller, Georges

doi:10.1139/v78-406

Cited by 11 publications

(4 citation statements)

References 4 publications

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“…They contain quaternized phosphorus in a five-membered unsaturated heterocycle. Some phospholium salts have been prepared previously but they were quaternized only with short alkyl chains, e.g., methyl or benzyl [47,48]. Therefore, the compounds synthesized and characterized here represent a unique type of cationic surfactants.…”

Section: Resultsmentioning

confidence: 99%

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč

Devı́nsky

Pisárčik

et al. 2016

J Surfact & Detergents

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A series of novel phospholium amphiphilic compounds with straight alkyl chains with different numbers of carbon atoms (12,14,15,16,17,18) were synthesized. The quaternary phosphorus, phosphonium cation, is incorporated into a five-membered heterocyclic ring. Their physicochemical properties were investigated by measurements of surface tension, conductivity and dynamic light scattering. The critical micelle concentration (c M ), the surface tension value at the c M (c cmc ), the surface area at the surface saturation per head group (A cmc ), the ionization degree of micelle (a), the free energy of micellization (DG°m ic ), and hydrodynamic diameter (d h ) were determined. Antimicrobial activity was tested against bacteria and yeast. The structure-activity relationship was determined. 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.2 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6(0), 29.6(4), 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.6 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.9 (d, 1 J CP = 83.9 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.6 (d, 2 J CP = 10.7 Hz, Ph C ortho ), 134.6 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.4 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -H NMR (CDCl 3 , TMS) d: 0.88 (t, 3 J H,H = 6.7 Hz, 3H, CH 3 of alkyl chain), 1.13-1.38 (m, 22H, 11 9 CH 2 of alkyl chain), 1.38-1.62 (m, 4H, b, c CH 2 of alkyl chain) 2.29 (s, 6H, 2 9 = C-CH 3 ), 3.08-3.22 (m, 2H, a CH 2 of alkyl chain), 7.08 (d, 2 J HP = 30.9 Hz, 2H, = CHP), 7.54-7.61 (m, 2H, Ph H meta ), 7.61-7.75 (m, 1H, Ph H para ), 8.15-8.23 (m, 2H, Ph H ortho ); 13 C NMR (CDCl 3 , TMS) d: 14.1 (CH 3 of alkyl chain), 18.5 (d, 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.1 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6, 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.4 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.8 (d, 1 J CP = 83.8 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.5 (d, 2 J CP = 10.4 Hz, Ph C ortho ), 134.7 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.5 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -

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Section: Resultsmentioning

confidence: 99%

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč

Devı́nsky

Pisárčik

et al. 2016

J Surfact & Detergents

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“…No successful example of selective reduction of butadienylphosphine oxides into butadienylphosphines could be found in the literature. For example, it was reported that the reduction of 1,3‐butadienyldiphenylphosphine oxide with phenylsilane led to double bond hydrogenation 10a. Other reducing agents (LiAlH 4 , HSiCl 3 , Si 2 Cl 6 ) also proved to be unsuitable for the chemoselective conversion into butadienylphosphines 16.…”

Section: Methodsmentioning

confidence: 99%

Recyclable Porous Polymer‐Supported Copper Catalysts for Glaser and Huisgen 1,3‐Diolar Cycloaddition Reactions

Sun

et al. 2013

Chemistry An Asian Journal

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A family of polymer-attached phenanthrolines was prepared from solvothermal copolymerization of divinylbenzene with N-(1,10-phenanthroline-5-yl)acrylamide in different ratios. The polymer-supported copper catalysts were obtained through typical impregnation with copper(II) salts. The polymers and supported copper catalysts have been characterized by N2 adsortion, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and thermogravimetric analysis (TG); they exhibit a high surface area, hierarchical porosity, large pore volume, and high thermal and chemical stabilities. The copper catalyst has proved to be highly active for Glaser homocoupling of alkynes and Huisgen 1,3-diolar cycloaddition of alkynes with benzyl azide under mild conditions at low catalyst loading. The heterogeneous copper catalyst is more active than commonly used homogeneous and nonporous polystyrene-supported copper catalysts. In particular, the catalyst is easily recovered and can be recycled at least ten times without any obvious loss in catalytic activity. Metal leaching was prevented due to the strong binding ability of phenanthroline and products were not contaminated with copper, as determined by ICP analysis.

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“…The best documented ring-opening reaction takes place upon hydrolysis of phospholium salts (Scheme 23.24) [72,73]. In the transient hydroxyphosphorane, the phosphole ring probably occupies a axial-equatorial position, leading to cleavage of the elongated axial PÀC bond.…”

Section: Ring Openings and Expansionsmentioning

confidence: 99%

Phosphorus Heterocycles

Mathey

2011

Modern Heterocyclic Chemistry

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Figure 23.1 The three isomers of the phosphole system (A-C) and the phospholide ion (D).2072j 23 Phosphorus Heterocycles shown with 1-alcoxyphospholes, which are relatively flat with a negligible delocalization [12]. Contrary to phospholes, the structure of phospholide ions reflects their high aromaticity. For example, the planar 2,3,4,5-tetramethylphospholide with Li(TMEDA) þ as the counterion displays the following parameters [13]: P-C, 1.715 A ; C¼C, 1.396 A ; CÀC, 1.424 A ;

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Hydrolyse des sels de phospholium monomères: Préparation et propriétés des oxydes de 1,3-diénylphosphines

Cited by 11 publications

References 4 publications

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Recyclable Porous Polymer‐Supported Copper Catalysts for Glaser and Huisgen 1,3‐Diolar Cycloaddition Reactions

Phosphorus Heterocycles

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