- Long sought synthesis of quaternary phosphonium salts from phosphine oxides: Inverse reactivity approach
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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.
- Vetter, Anna C.,Nikitin, Kirill,Gilheany, Declan G.
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p. 5843 - 5846
(2018/06/13)
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- Ethyl triphenyl phosphonium chloride preparation method
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The invention provides an ethyl triphenyl phosphonium chloride preparation method, which comprises: (1) adding triphenyl phosphine to an organic solvent, adding ethyl chloride in a dropwise manner, heating to a temperature of 120-160 DEG C after the adding, adjusting the reaction pressure to 8-12 kg/cm, and carrying out a thermal insulation reaction for 30-40 h; (2) after completing the thermal insulation reaction, cooling to a room temperature, reducing the pressure to a normal pressure, and carrying out centrifugation on the material obtained after the reaction; and (3) drying the centrifugal precipitate so as to obtain the ethyl triphenyl phosphonium chloride. According to the present invention, with the method, the yield is up to more than 94%, and the purity is up to more than 99%.
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Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023-0025
(2017/03/14)
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- One alkyl triphenyl substituted group based phosphonium salt preparation method and application
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The invention discloses a one alkyl triphenyl substituted group based phosphonium salt preparation method and application. The preparation method includes that a one alkyl triphenyl phosphonium salt halide I is obtained through reaction of several alkyl h
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Paragraph 0033-0040
(2017/09/12)
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- Reactions with Phosphine Alkylenes, XLV. Reactions of Alkylidenetriphenylphosphoranes with Tetramethylformamidinium Chloride. Synthesis of triphenylphosphonium Chloride and (Formylalkylidene)triphenylphosphoranes
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Phosphonium ylides 1 react with tetramethylformamidinium chloride (2) to form enamine phosphonium chlorides 8 and the formic orthoamide 7.The salts 8 show temperature depending 1H NMR spectra with respect to the protons of the dimethylamino group (hindered rotation around the C - N(CH3)2 bond).Treatment of 8 with acids and subsequently with bases gives rise to the formation of the formyl ylides 19. 8a is deprotonated with sodium amide to give the phosphaallene ylide 20, which reacts with water to yield the phosphane oxide 21, and with methyl iodide stereospecifically to form 8b.
- Bestmann, Hans Juergen,Schmid, Guenter,Oechsner, Helmut,Ermann, Peter
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p. 1561 - 1571
(2007/10/02)
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- Reactions with Phosphine Alkylenes, XLII. A Sequence for the Preparation of Acetylenes Starting from Carboxylic Chlorides and Phosphorus Ylides via 1,2-Diketones.
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Phosphorus ylides 1 and carboxylic chlorides 2 react with transylidation to give acyl ylides 3 which are oxidized with the adduct of ozone to triphenyl phosphite to yield 1,2-diketones 5.These are converted into the bis(hydrazones) 6 which are oxidized with O2/CuCl in pyridine giving acetylenes 7.
- Bestmann, Hans Juergen,Kumar, Kamlesh,Kisielowski, Lothar
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p. 2378 - 2382
(2007/10/02)
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