Mass spectrometry and quantum chemical studies of the reaction of divinyl telluride with secondary phosphine sulfides: Synthesis of adducts

Гусарова, Н. К.; Чернышeва, Н. А.; Клыба, Л. В.; Шагун, В. А.; Yas’ko, S. V.; Смирнов, В. И.; Трофимов, Б. А.

doi:10.1016/j.jorganchem.2013.07.050

Journal of Organometallic Chemistry

2013

DOI: 10.1016/j.jorganchem.2013.07.050

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Mass spectrometry and quantum chemical studies of the reaction of divinyl telluride with secondary phosphine sulfides: Synthesis of adducts

Н. К. Гусарова

Н. А. Чернышeва

Л. В. Клыба

et al.

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Cited by 5 publications

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References 12 publications

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“…Reactions of this type have been successfully realized under radical conditions by the example of divinyl [1], diallyl [2,3], trivinyl [4], tetravinyl [5] ethers, divinyl chalcogenides [6][7][8][9], as well as tris(4-vinylbenzyl)phosphine oxide [10]. As a result, promising polydentate ligands for metal complexes, including metallacrown ethers [1,[11][12][13] have been synthesized.…”

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Reaction of secondary phosphine chalcogenides with diallylamine

et al. 2014

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Diphenyl-or bis(2-phenylethyl)phosphine sulfides and -phosphine selenides react with diallylamine under radical initiation (UV or AIBN) to afford the corresponding diadducts and tetrahydropyrrolylmethyl phosphine chalcogenides. The yield and the ratio of the products depend on the structure of the starting secondary phosphine chalcogenides.Addition of secondary phosphines and phosphine chalcogenides to polyalkenes is a convenient atomeconomic approach to the synthesis of polyphosphines and polyphosphine chalcogenides including their functional derivatives. Reactions of this type have been successfully realized under radical conditions by the example of divinyl [1], diallyl [2, 3], trivinyl [4], tetravinyl [5] ethers, divinyl chalcogenides [6-9], as well as tris(4-vinylbenzyl)phosphine oxide [10]. As a result, promising polydentate ligands for metal complexes, including metallacrown ethers [1, 11-13] have been synthesized.At the same time, there are no data in the literature on the reaction of diallylamine with secondary phosphine chalcogenides, although substituted diallylamines react with diphenylphosphine oxide (AIBNinitiation) [2] and diphenylphosphine sulfide (microwave activation) [3] to give cyclic adducts, phosphoruscontaining pyrrolidines (Scheme 1).In the present work we have studied for the first time the radical addition of secondary phosphine sulfides and phosphine selenides to diallylamine in order to develop a general convenient atom-economic method of the synthesis of functional tertiary phosphine chalcogenides containing an amino group.Diphenylphosphine sulfide (I) turned out to react with diallylamine (in the ratio 2 : 1) in benzene or dioxane at UV irradiation (200W Hg arc Lamp) or in the presence of AIBN (5 wt %, 60-65 о С) in 2-2.5 h to give diadduct II as the main product (the isolated yield 52%). For the equimolar ratio of the reagents, compound II is also the main product (Scheme 2).

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Reaction of secondary phosphine chalcogenides with diallylamine

et al. 2014

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Facile Non‐Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes

Малышева¹,

Гусарова²,

Artem’ev³

et al. 2014

Eur J Org Chem

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An atom‐economic green synthesis of tertiary phsophine sulfides has been developed based on catalyst‐ and solvent‐free addition of secondary phosphine sulfides to diverse terminal and internal alkenes (hept‐1‐ene, cyclohexene, styrenes, allyl alcohol, vinyl ethers, vinyl sulfides, vinyltrimethylsilane, 1‐vinylimidazoles, vinyl acetate). The reaction proceeds under mild conditions (80 °C, without solvent, 4–45 h) to afford chemo‐ and regioselectively the corresponding anti‐Markovnikov adducts in excellent to quantitative yields (50–99 %).

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Organophosphorus chemistry based on elemental phosphorus: advances and horizons

Гусарова¹,

Трофимов²

2020

Russ. Chem. Rev.

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The results of studies on the application of elemental phosphorus for the synthesis of important organophosphorus compounds are surveyed and summarized. Currently, this trend represents a synthetically, environmentally and technologically attractive alternative to classical organophosphorus chemistry based on toxic and corrosive phosphorus chlorides. Direct phosphination and phosphinylation of organic compounds with elemental phosphorus (discussed in the first part of the review) basically extend the range of available phosphines, phosphine chalcogenides and phosphinic acids and provides further development of their synthetic potential (discussed in the second part of the review). It is shown that the breakthrough in this area is largely due to the discovery of reactions of elemental phosphorus (white and red) with various electrophiles in superbasic suspensions and emulsions derived from alkali metal hydroxides and to the development of electrochemical, electrocatalytic and catalytic activation of white phosphorus. The bibliography includes 299 references.

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Mass spectrometry and quantum chemical studies of the reaction of divinyl telluride with secondary phosphine sulfides: Synthesis of adducts

Cited by 5 publications

References 12 publications

Reaction of secondary phosphine chalcogenides with diallylamine

Reaction of secondary phosphine chalcogenides with diallylamine

Facile Non‐Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes

Organophosphorus chemistry based on elemental phosphorus: advances and horizons

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