Facile Synthesis of Hyper‐Branched Tetraphosphanes and Tetraphosphane Chalcogenides

Трофимов, Б. А.; Малышева, С. Ф.; Белогорлова, Н. А.; Kuimov, Vladimir A.; Albanov, A. I.; Гусарова, Н. К.

doi:10.1002/ejoc.200900382

Cited by 13 publications

(5 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Treatment of C(CH 2 OCHCH 2 ) 4 with HP(CH 2 CH 2 C 6 H 5 ) 2 gave (90%) C[CH 2 OCH 2 CH 2 P(CH 2 CH 2 C 6 H 5 ) 2 ] 4 , and addition of 1-bromomethylnaphthylene gave (99%) C[CH 2 OCH 2 CH 2 P + (CH 2 CH 2 C 6 H 5 ) 2 (CH 2 C 10 H 7 )] 4 (4Br − ) …”

Section: → 3 P-branchedmentioning

confidence: 99%

Dendrimers Derived from 1 → 3 Branching Motifs

2010

View full text Add to dashboard Cite

Section: → 3 P-branchedmentioning

confidence: 99%

Dendrimers Derived from 1 → 3 Branching Motifs

2010

View full text Add to dashboard Cite

“…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.…”

mentioning

confidence: 99%

Reaction of secondary phosphine chalcogenides with diallylamine

et al. 2014

View full text Add to dashboard Cite

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).

show abstract

“…A preliminary application of this strategy was reported with examples of divi-nyl ethers of diols 17 and the tetravinyl ether of pentaerithritol. 18 The high chemo-and regioselectivity of the hydrophosphination found deserves special consideration. Indeed, as noted above, neither expected cyclizations nor oligomerizations were discernible in this hydrophosphination.…”

mentioning

confidence: 99%

Synthesis of Functional Tripodal Phosphines with Amino and Ether Groups by the Hydrophosphination of Trivinyl Ethers with Secondary Phosphines

et al. 2014

View full text Add to dashboard Cite

A one-pot, atom-economic, metal-and halogen-free synthesis of functional triphosphines with nitrogen and (or) oxygen atoms as additional weaker coordinating sites (new hemilabile ligands) through exhaustive addition of secondary phosphines to available trivinyl ethers of aminotriols and triols has been developed. The reaction proceeds under free-radical conditions (UV irradiation or AIBN, with 3:1 reactant molar ratio) to give chemo-and regioselectively anti-Markovnikov triadducts to all three vinyloxy groups in good to excellent yields.

show abstract

Facile Synthesis of Hyper‐Branched Tetraphosphanes and Tetraphosphane Chalcogenides

Abstract: Novel families of hyper-branched tertiary tetraphosphanes, tetraphosphane sulfides, and tetraphosphane selenides were synthesized in 72-97 % yield by treating secondary phosphanes, phosphane sulfides, and phosphane selenides with

Cited by 13 publications

References 42 publications

Dendrimers Derived from 1 → 3 Branching Motifs

Dendrimers Derived from 1 → 3 Branching Motifs

Reaction of secondary phosphine chalcogenides with diallylamine

Synthesis of Functional Tripodal Phosphines with Amino and Ether Groups by the Hydrophosphination of Trivinyl Ethers with Secondary Phosphines

Contact Info

Product

Resources

About