2304-24-7Relevant articles and documents
Unravelling the mechanism of toxicity of alkyltributylphosphonium chlorides in Aspergillus nidulans conidia
Petkovic, Marija,Hartmann, Diego O.,Adamova, Gabriela,Seddon, Kenneth R.,Rebelo, Luis Paulo N.,Pereira, Cristina Silva
, p. 56 - 63 (2012)
The mechanism of toxicity of alkyltributylphosphonium chlorides [P 4 4 4 n]Cl (n = 1, 3-8, 10, 12 or 14) in conidia of the filamentous fungus Aspergillus nidulans is reported. Systematic elongation of one of the alkyl substituents resulted generally in higher toxicity, as defined by their inhibitory and lethal effects. In this study, fluorescence microscopy is proposed as a direct method for assessing the impact of ionic liquids on the plasma membrane integrity. Data were complemented by microscopic evaluation of the conidia cell wall and morphology. The higher toxicity of phosphonium ionic liquids carrying long alkyl substituents is most likely due to their strong interaction with the conidia cellular boundaries. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Exploring an Umpolung strategy for quaternization of phosphorus
Vetter, Anna C.,Nikitin, Kirill,Gilheany, Declan G.
, p. 339 - 342 (2019/03/07)
We propose a new, potentially widely-applicable, Umpolung approach for the synthesis of quaternary phosphonium salts R3PR1 X (X = Cl, Br) from phosphine oxides R3PO. The new organic group R1 is introduced via nucleophilic attack on an intermediate halophosphonium salt using a Grignard reagent R1MgX and replaces the traditional phosphine quaternization approach. Consequently, the new method does not suffer from the limited availability of many parent phosphines and is much faster than standard quaternization.
Long sought synthesis of quaternary phosphonium salts from phosphine oxides: Inverse reactivity approach
Vetter, Anna C.,Nikitin, Kirill,Gilheany, Declan G.
, p. 5843 - 5846 (2018/06/13)
Quaternary phosphonium salts (QPS), a key class of organophosphorus compounds, have previously only been available by routes involving nucleophilic phosphorus. We report the realisation of the opposite approach to QPS utilising phosphine oxides as the electrophilic partner and Grignard reagents as nucleophiles. The process is enabled through the crucial intermediacy of the derived halophosphonium salts. The route does not suffer from the slow kinetics and limited availability of many parent phosphines and a broad range of QPS were prepared in excellent yields.
Alkyltributylphosphonium chloride ionic liquids: Synthesis, physicochemical properties and crystal structure
Adamova, Gabriela,Gardas, Ramesh L.,Nieuwenhuyzen, Mark,Puga, Alberto V.,Rebelo, Luis Paulo N.,Robertson, Allan J.,Seddon, Kenneth R.
experimental part, p. 8316 - 8332 (2012/08/08)
A series of alkyltributylphosphonium chloride ionic liquids, prepared from tributylphosphine and the respective 1-chloroalkane, CnH 2n+1Cl (where n = 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12 or 14), is reported. This work is a continuation of an extended series of tetraalkylphosphonium ionic liquids, where the focus is on the variability of n and its impact on the physical properties, such as melting points/glass transitions, thermal stability, density and viscosity. Experimental density and viscosity data were interpreted using QPSR and group contribution methods and the crystal structure of propyl(tributyl)phosphonium chloride is detailed. The Royal Society of Chemistry 2012.
A direct synthesis of vinylphosphonium salts from α-trimethylsilyl ylides and non-enolizable aldehydes
McNulty, James,Das, Priyabrata
body text, p. 8469 - 8472 (2009/10/23)
A direct synthesis of vinylphosphonium salts from α-trimethylsilyl ylides and non-enolizable aldehydes was reported. The vinylphosphonium salt was isolated in 90% yield and with high stereoselectivity favoring the (E)-olefin. High chemoselectivity observed favoring Peterson elimination over Wittig-type elimination and general stereoselectivity favoring (E)-vinylphosphonium salts require free-rotation about the central C-C bond of a betaine intermediate. The results show that the clean synthesis of the stable silylphosphonium iodide salt, subsequent generation of its yield derivative, and stoichiometric reaction with aldehydes at low temperature allows highly selective vinylphosphonium salt formation. It is also seen that the (E)-vinylphosphonium stereoselectivity is due to kinetic control involving Peterson syn-elimination from the erythro betaine.
Reaktion von Acetyl-Uebergangsmetallkomplexen mit Phosphor-Yliden - ein weiteres Beispiel zur Halogenid/Metallat-Analogie
Malisch, Wolfgang,Blau, Herbert,Haaf, Franz Jakob
, p. 2956 - 2970 (2007/10/02)
The reaction of the acetyl metal complexes LnM-C(O)CH3Mo> with the phosphorus ylides (CH3)3P=CH2, C2H5(CH3)2P=CH2, (C2H5)3P=CHCH3 and (C4H9)3P=CH2 in the ratio 1:2 yields the corresponding acetyl-substituted ylides R3P=CR'C(O)CH3 3a - d (R = CH3, C2H5, n-C4H9; R' = H, CH3) and phosphonium metalates 4a - d, 6a, b via heterolysis of the Fe-C-?-bond and transylidation.With CH3C(O)Cl an analogous way of reaction is observed, which however can be repeated to give the diacetyl ylides R3P=C(COCH3)2 8a, b (R = CH3, n-C4H9).The new compounds are characterized by spectroscopic methods (NMR, IR) and further reactions.
