Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives

Гусарова, Н. К.; Verkhoturova, S. I.; Kazantseva, T. I.; Mikhailenko, V. L.; Arbuzova, S. N.; Трофимов, Б. А.

doi:10.1016/j.mencom.2011.01.007

Cited by 11 publications

(3 citation statements)

References 24 publications

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“…The highest activity showed a redox monomer М 2 and its polymer RP 2 . Increasing the concentration of BuOH to 109 mmol, the temperature to 70 °C in iodine alcohol solutions RP 2 and M 2 contributed to complete conversion of РН 3 forming 10-64% dialkylphosphite and 36-52% trialkylphosphate (experiments [8][9][10][11].…”

Section: Tablementioning

confidence: 99%

“…Synthesis, on the basis of PH 3 , is used very rarely and it is not realized in the industry because there are no effective technological methods of its obtaining. Trofimov with colleagues [7][8][9][10][11][12][13][14] developed in recent years convenient methods of synthesis of organophosphorus compounds on the basis of phosphine, generated in the water and organic medium from red phosphorus in the presence of the superstrong bases. Phosphin can be used for obtaining various OPhC which are important supplementary reagents, construction blocks, semi-products, and also ligands for metalcomplex catalysts, extragents and аntipyrenes.…”

Section: Introductionmentioning

confidence: 99%

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The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

et al. 2012

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This article presents the synthesis of phosphoric acid esters from phosphoric hydrogen РН 3 and aliphatic alcohols. The process is based on the oxidation of phosphine by quinones and redox polymers on the basis of mono-and disubstituted quinoid derivatives of monoethanolamine vinyl ether. Molecular iodine is used as a catalyst. Two-, three-, four-and multicomp onent systems are studied in order to determine optimal conditions of the oxidation of phosphine quinones and repoxpolymers on their basis. The rate and selectivity of reaction were monitored by the absorption of РН 3 . As alcohols used aliphatic alcohols: BuOH, PrOH, EtOH, MeOH. Organophosphorus compounds were analyzed by a chromatographic method. It was established that alcohol solutions of individual components of reactionary system (quinones, redox ionites or iodine) are characterized by a low activity in relation to phosphine. Organophosphorus compounds are formed in insignificant quantities. In the mixed alcohol solution of benzoquinone takes place PH 3 oxidation forming trialkylphosphates. Conversion of phosphine constitutes 80-100%. Increasing the concentration of reagents of catalytic system has a positive effect on the process as a whole. Similar patterns were obtained when redox monomers and polymers on the base of quinones in the presence of iodine were used as oxidants. Esters of phosphoric acid -dialkylphosphites and esters of phosphorous acid -trialkylphosphates were identified as organophosphorus compounds. By selecting a redox agent in a zone of the catalysis it is possible to direct process in the desirable direction. The most activity in the oxidation of phosphine by iodine-alcohol solutions of quinoid monomers and polymers, is exhibited by 2-[N-(2-vinyloxy) ethyl]amino-NQ and polymer on their basis. Results of our experiments and literature data on oxidation-reduction processes with participation of iodine and quinones in organic solutions allowed to propose the separate oxidation-reduction mechanism of formation of organophosphorus compounds. In investigated multicomponent systems, the synergetic effect is manifested which is reached at the expense of distribution of oxidation-reduction functions among iodine, quinones and its derivatives. In this report, for the first time, it is established reactionary ability of quinones and redox ionites on their basis in an oxidizing alkoxylation of phosphine to valuable esters of acids of phosphorus. Reaction can be used for purification of exhaust and technological gases from phosphine and its utilization.

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Section: Tablementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

et al. 2012

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“…Phosphine (PH 3 ) is another possible feedstock used to prepare P-containing monomers, without the aid of chloride, due to its three reactive P–H bonds. 11 However, PH 3 is a highly toxic and flammable gas, therefore special attention should be paid to its use. As a result, only a few reports have been published on the use of PH 3 as a feedstock for the preparation of P-containing polymers.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent phosphine oxide-containing hyperbranched polyesters: design, synthesis and their application for Fe³⁺detection

et al. 2023

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Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

Murai

2014

Patai's Chemistry of Functional Groups

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This chapter describes syntheses, structures, and reactions of the compounds with phosphorus‐selenium double bonds and with at least one carbon‐phosphorus single bond and of their heavier congeners. Among them, phosphane selenides have been the most deeply studied and used as Lewis base catalysts, metal ligands, molecular sensors, and stating materials leading to selenium‐containing nanoparticles. The coupling constants between the phosphorus and selenium atoms are informative on the basicity of the phosphanes. Phosphinoselenoic acid chlorides and secondary phosphanes are frequently used precursors to give a range of phosphinoselenoic acid derivatives, whereas selenation of dichlorophosphanes leads to phosphonoselenoic acid dichlorides, which are converted to a variety of acid derivatives. The selenation of phosphinites also gives phosphinoselenoic acid O ‐esters. Stereochemical course of the substitution reaction at P ‐chiral phosphorus center in the substitution reaction has been elucidated. Some reactions of dimers of diselenoxophosphanes such as Woollin's reagent are also shown. The chapter finally describes examples of phosphane tellurides, arsenic, antimony, and bismuth isologues of phosphane selenides, although these are fewer.

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Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives

Cited by 11 publications

References 24 publications

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

Fluorescent phosphine oxide-containing hyperbranched polyesters: design, synthesis and their application for Fe³⁺detection

Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

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Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives

Cited by 11 publications

References 24 publications

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

Fluorescent phosphine oxide-containing hyperbranched polyesters: design, synthesis and their application for Fe3+detection

Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

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Fluorescent phosphine oxide-containing hyperbranched polyesters: design, synthesis and their application for Fe³⁺detection