3582-82-9

Usage

Uses

Used in Organic Synthesis:
Phosphine oxide, diphenyl[(1E)-2-phenylethenyl]is utilized as a reagent in organic synthesis, where it aids in the formation of new chemical bonds and the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable component in the development of novel organic compounds.
Used in Catalysts for Reactions:
In addition to its role as a reagent, Phosphine oxide, diphenyl[(1E)-2-phenylethenyl]also serves as a catalyst in various chemical reactions. Its ability to lower the activation energy of reactions and increase reaction rates makes it an essential tool in the field of catalysis.
Used in Materials Science:
Phosphine oxide, diphenyl[(1E)-2-phenylethenyl]has been studied for its potential applications in materials science. Its unique properties may contribute to the development of new materials with specific characteristics, such as improved stability, reactivity, or selectivity.
Used in Medicinal Chemistry:
Phosphine oxide, diphenyl[(1E)-2-phenylethenyl]has also been investigated for its potential use in medicinal chemistry. Its unique structure and reactivity may enable the development of new pharmaceutical compounds with novel therapeutic properties.
However, it is crucial to handle Phosphine oxide, diphenyl[(1E)-2-phenylethenyl]with caution, as it may pose health and environmental hazards if not properly managed and disposed of. Proper safety measures and disposal protocols should be followed to minimize any potential risks associated with its use.

Upstream product

• 7608-18-6 phenylethynyl diphenylphosphine oxide 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 65567-06-8 lithium diphenylphosphide 
• 55743-31-2 (1-chlorovinyl)diphenylphosphine oxide 
• 23402-69-9 lithium diphenylcuprate 
• 122601-15-4 2-Fluoro-2,2,4-triphenyl-3-trimethylsilanyl-2λ⁵-[1,2]oxaphosphetane 
• 122601-31-4 fluorodiphenylphosphonium-(trimethylsilyl)methylide 
• 100-52-7 benzaldehyde 
• 76002-35-2 C₁₉H₁₇OPTe 
• 76002-34-1 (Diphenyl-phosphinoylmethyl)-diphenyl-stibane 
• 149210-90-2 Diphenylphosphinylmethanphosphonsaeurediisopropylester 
• 149210-92-4 Benzol-diphenylphosphinylmethanphosphinsaeureisopropylester 
• 2071-21-8 bis(diphenylphosphoryl)methane 
• 683-08-9 Diethyl methylphosphonate 

Downstream Products

• 372166-93-3 (E)-2-diphenylphosphinyl-2-trimethylsilylstyrene 
• 3582-84-1 (2-phenylethyl)diphenylphosphine oxide 
• 3583-85-5 (+/-)-1,2-bis(diphenylphosphino)phenylethane P,P'-dioxide 
• 3582-83-0 diphenyl-trans-β-styrylphosphine sulfide 
• 1261158-16-0 [2-phenyl-2-(phenylthio)ethyl]diphenylphosphane oxide 
• 167865-53-4 (E)-1-tert-butyl(diphenyl)silyl-2-phenylethene 
• 1261157-97-4 [2-(tert-butyldiphenylsilyl)-2-phenylethyl]diphenylphosphane oxide 
• 64788-85-8 dimethyl-phenyl-((E)-styryl)-silane 
• 1261157-96-3 [2-(dimethylphenylsilyl)-2-phenylethyl]diphenylphosphane oxide 
• 203574-98-5 (1'R)-N-Benzyl-N-(1'-phenylethyl)-2-diphenylphosphinoyl-1-phenylethylamine 

Relevant academic research and scientific papers

Heterogeneous Catalytic Method for the Copper(II)-Catalysed Addition of H-Phosphinates and Secondary Phosphine Oxides to Phenylacetylene

Copper(II) on 4?? molecular sieve was found to be an efficient heterogeneous catalyst in the addition of different H-phosphinates and secondary phosphine oxides to phenylacetylene. All hydrophosphinylation reactions were completely regioselective, as only β-isomers were formed, and the E-alkenylphosphinates and E-alkenylphosphine oxides were synthesized in moderate to excellent yields. The catalyst could be reused multiple times in the reaction. Graphic Abstract: [Figure not available: see fulltext.]

Cerium(IV)-Promoted Phosphinoylation-Nitratation of Alkenes

A Cerium(IV)-promoted phosphinoylation-nitratation of alkenes is established under mild conditions. In this process, Ceric ammonium nitrate (CAN) acts as a cheap phosphorus-radical initiator, as well as a nitrate donor. Various β-nitrooxyphosphonates are

STARKE ERLEICHTERUNG DER CARBONYLOLEFINIERUNG MIT ORGANOSCHWERMETALLREAGENZIEN DURCH EINE DIPHENYLPHOSPHORYLGRUPPE IM REAGENZ

Carbonyl olefination with a lithiomethane, having besides the group -P(O)Ph2 at the methane C-atom an organo-heavy-metal group, occurs at low temperatures to give exclusively diphenylphosphoryl substituted olefins.

Oxidative Addition of Secondary Phosphine Oxides through Rh(I) Center: Hydrido-Phosphinito-Rh(III) Complexes and their Catalytic Activity in Hydrophosphinylation of Alkynes

The reaction of [Rh(μ-Cl)(cod)]2 with diimines, differing in their steric and electronic properties, and with diphenylphosphine oxide leads to the oxidative addition products, hydrido-phosphinito-Rh(III) complexes {Rh(PPh2OH)(PPh2O)(NN)(H)Cl} (1), stabilized by the formation of a hydrogen bonded phosphinous acid-phosphinito quasi-chelate [(PO???HOP)-κ2P]. Exchange of hydride by chloride to afford {Rh(PPh2OH)(PPh2O)(NN)Cl2} (2) occurs in hydrido complexes containing low steric hindrance diimines and is inhibited for complexes containing encumbered diimines. Complexes 1 react with BF3?OEt2 with exchange of the acidic proton by BF2, and transformation of the quasi-chelating PO???HOP into a chelating PO-BF2-OP ligand in {Rh{(PPh2O)2BF2}(NN)(H)Cl} (3). The reaction of [Rh(μ-Cl)(nbd)]2 or [Rh(acac)(nbd)] with diphenylphosphine oxide leads to coordinatively unsaturated nortricyclyl-phosphinito-Rh(III) complexes, {Rh(PPh2OH)(PPh2O)(ntyl)(μ-Cl)}2 (4) or {Rh(PPh2OH)(PPh2O)(ntyl)(acac)} (6), respectively. Their reaction with BF3?OEt2 results in the corresponding {Rh{(PPh2O)2BF2}(ntyl)(μ-Cl)}2 (5) or {Rh{(PPh2O)2BF2}(ntyl)(acac)} (7). Some of these new complexes have shown catalytic activity in hydrophosphinylation of alkynes, with {Rh(PPh2OH)(PPh2O)(NN)(H)Cl} containing encumbered NN being efficient and regioselective catalysts in the hydrophosphinylation of phenylacetylene with diphenylphosphine oxide to produce (E)-diphenyl(styryl)phosphine oxide.

Knoevenagel Condensation of Phosphinoylacetic Acids with Aldehydes: An Efficient One-Pot Strategy for the Synthesis of P-Functionalized Alkenyl Compounds

A wide range of commercially available aldehydes have been applied to Knoevenagel condensation reaction to give E -alkenylphosphine oxides and vinylphosphine oxides. The readily available phosphinoylacetic acids derived from P(O)-H compounds were used as the starting materials in the reaction, providing a highly stereoselective and efficient method for constructing α,β-unsaturated phosphine oxides. Moreover, this simple and practical procedure provides an alternative and more environmentally friendly synthesis strategy for this type of P-functionalized alkenyl compounds.

Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds

The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

Cobaloxime Catalysis: selective synthesis of alkenylphosphine oxides under visible light

Direct activation of H-phosphine oxide to react with an unsaturated carbon-carbon bond is a straightforward approach for accessing alkenylphosphine oxides, which shows significant applications in both synthetic and material fields. However, expensive metals and strong oxidants are typically required to realize the transformation. Here, we demonstrate the utility of earth-abundant cobaloxime to convert H-phosphine oxide into its reactive radical species under visible light irradiation. The radical species thus generated can be utilized to functionalize alkenes and alkynes without any external photosensitizer and oxidant. The coupling with terminal alkene generates E-alkenylphosphine oxide with excellent chemo- A nd stereoselectivity. The reaction with terminal alkyne yields linear E-alkenylphosphine oxide via neutral radical addition, while addition with internal ones generates cyclic benzophosphine oxides and hydrogen. Mechanistic studies on radical trapping experiments, electron spin resonance studies, and spectroscopic measurements confirm the formation of phosphinoyl radical and cobalt intermediates that are from capturing the electron and proton eliminated from H-phosphine oxide. The highlight of our mechanistic investigation is the dual role played by cobaloxime, viz., both as the visible light absorber to activate the P(O)-H bond as well as a hydrogen transfer agent to influence the reaction pathway. This synergetic feature of the cobaloxime catalyst preforming multiple functions under ambient condition provides a convergent synthetic approach to vinylphosphine oxides directly from H-phosphine oxides and alkenes (or alkynes).

Cobaloxime Catalysis: Selective Synthesis of Alkenylphosphine Oxides under Visible Light

Direct activation of H-phosphine oxide to react with an unsaturated carbon-carbon bond is a straightforward approach for accessing alkenylphosphine oxides, which shows significant applications in both synthetic and material fields. However, expensive metals and strong oxidants are typically required to realize the transformation. Here, we demonstrate the utility of earth-abundant cobaloxime to convert H-phosphine oxide into its reactive radical species under visible light irradiation. The radical species thus generated can be utilized to functionalize alkenes and alkynes without any external photosensitizer and oxidant. The coupling with terminal alkene generates E-alkenylphosphine oxide with excellent chemo- and stereoselectivity. The reaction with terminal alkyne yields linear E-alkenylphosphine oxide via neutral radical addition, while addition with internal ones generates cyclic benzophosphine oxides and hydrogen. Mechanistic studies on radical trapping experiments, electron spin resonance studies, and spectroscopic measurements confirm the formation of phosphinoyl radical and cobalt intermediates that are from capturing the electron and proton eliminated from H-phosphine oxide. The highlight of our mechanistic investigation is the dual role played by cobaloxime, viz., both as the visible light absorber to activate the P(O)-H bond as well as a hydrogen transfer agent to influence the reaction pathway. This synergetic feature of the cobaloxime catalyst preforming multiple functions under ambient condition provides a convergent synthetic approach to vinylphosphine oxides directly from H-phosphine oxides and alkenes (or alkynes).

Cycloaddition of Vinylphosphine Oxides to α-Oxy- o-xylylene as a route to Phosphorylated Naphthyl and Biaryl Scaffolds

α-Oxy-o-xylylene, a highly reactive diene readily accessible from benzocyclobutenol, undergoes Diels-Alder reaction with vinylphosphine oxides, yielding the corresponding 2-phosphorylated 1-hydroxy-1,2,3,4-tetrahydronaphthalenes in excellent yields. Use of unsubstituted and trans-2-aryl-substituted vinylphosphine oxides leads to cycloadducts with complete regioselectivity and with cis/trans selectivity up to 19:1 in the most favorable case. In the case of P-stereogenic trans-2-aryl-substituted vinylphosphine oxides, a virtually complete chirality transfer from P to C can be achieved. Dehydration and aromatization of the obtained cycloadducts bearing the resolved P-stereogenic phosphinoyl groups can be carried out to afford the valuable P-stereogenic and axially chiral phosphorylated 1,2′-binaphthyl ring system. Cases of restricted rotation around Csp3-Csp2 single bond in some tetrahydronaphthalene cycloadducts have also been revealed.

Ceric(IV) Ammonium Nitrate Mediated Phosphorylation of Alkenes: Easy Access to (E)-Vinylphosphonates

An inexpensive Ceric(IV) ammonium nitrate mediated phosphorylation of alkenes has been developed. Without adding expensive metals and other additives, various (E)-alkenylphosphane oxides are obtained through an easy route in a one-pot manner. Preliminary