1733-57-9

Usage

Uses

Used in Chemical Synthesis:
DIPHENYLETHYLPHOSPHINE OXIDE is used as a reactant for the regioselective lactonization of unsymmetrical 1,4-diols. This application is particularly useful in the synthesis of complex organic molecules, as it allows for the selective formation of lactones with specific structural features.
Used in Catalyst Production:
DIPHENYLETHYLPHOSPHINE OXIDE is used as a reactant in the synthesis of a nanostructured dioxomolybdenum(VI) catalyst. This catalyst is specifically designed for liquid-phase epoxidation of olefins, a crucial reaction in the production of various chemicals and materials.
Used in Reducing Agents:
DIPHENYLETHYLPHOSPHINE OXIDE is used as a reducing agent for the reduction of tertiary phosphine oxides with DIBAL-H. This reaction is essential in the synthesis of various organic compounds, as it allows for the conversion of phosphine oxides into their corresponding phosphines.
Used in Organic Synthesis:
DIPHENYLETHYLPHOSPHINE OXIDE is used as a reagent in the Diphenylphosphineyl-mediated synthesis of ketones. This method involves the use of DIPHENYLETHYLPHOSPHINE OXIDE to facilitate the formation of carbonyl groups in organic molecules, which are important functional groups in many pharmaceuticals and other chemicals.
Used in Nucleophilic Aromatic Substitution:
DIPHENYLETHYLPHOSPHINE OXIDE is used as a reagent in the nucleophilic aromatic substitution of hydrogen by phosphorous stabilized carbanions. This reaction is a key step in the synthesis of various aromatic compounds, as it allows for the introduction of new functional groups onto the aromatic ring.
Used in Stereospecific Reduction:
DIPHENYLETHYLPHOSPHINE OXIDE is used as a reagent in the stereospecific reduction to form phosphines. This reaction is crucial in the synthesis of optically active phosphine compounds, which are important in various applications, including catalysis and materials science.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 3931, 1983 DOI: 10.1016/S0040-4039(00)94318-1

InChI:InChI=1/C14H15OP/c1-2-16(15,13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12H,2H2,1H3

Upstream product

• 719-80-2 Ethyl diphenylphosphinite 
• 1707-03-5 diphenyl-phosphinic acid 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 603-35-0 triphenylphosphine 
• 607-01-2 ethyl-diphenyl-phosphane 
• 932-92-3 cyclohexyl ethyl ether 
• 6399-81-1 triphenylphosphine hydrobromide 
• 75-07-0 acetaldehyde 
• 829-85-6 diphenylphosphane 
• 38828-07-8 diphenyl(α-hydroxy)ethylphosphine oxide 
• 55743-31-2 (1-chlorovinyl)diphenylphosphine oxide 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 778-66-5 1,1-diphenyl-1-propene 
• 13317-44-7 ethyl(phenyl)phosphinic acid 
• 59555-99-6 1-[1-(Diphenyl-phosphinoyl)-ethyl]-cyclohexanol 
• 63103-81-1 (1RS,2SR)-1-phenyl-2-(diphenylphosphinoyl)propan-1-ol 
• 4252-61-3 (1-methylpropyl)diphenylphosphane oxide 
• 63103-55-9 (E)-pent-3-en-2-yldiphenylphosphine oxide 
• 59627-82-6 (E)-4-Diphenylphosphinoyl-3-methyl-pent-2-en 
• 144863-58-1 -2-(1-Diphenylphosphinoylethyl)cyclopentanol 
• 144863-58-1 -2-(1-Diphenylphosphinoylethyl)cyclopentanol 
• 87109-17-9 1-diphenylphosphinoyl-4-(2-methyl-[1,3]dioxolan-2-yl)-propane 
• 146964-65-0 2-Diphenylphosphinoyl-6-hydroxyhexan-3-one 
• 146964-67-2 2-Diphenylphosphinoyl-7-hydroxyheptan-3-one 
• 119106-52-4 5-Diphenylphosphinoyl-4-oxohexanoic acid 
• 345661-79-2 3-diphenylphosphinoyl-1-phenylbutan-1-ol 

Relevant academic research and scientific papers

Novel Direct Deoxygenation of the Hydroxy Group of (1-Hydroxyalkyl)-diphenylphosphine Oxides

The hydroxyl group of (1-hydroxyalkyl)-diphenylphosphine oxides 1 is directly deoxygenated on treatment with phosphorus trichloride and iodides to give parent alkyl-diphenylphosphine oxides 2.

Correlation of the rates of solvolysis of chlorodiphenylphosphine using the extended grunwald-winstein equation

Specific rates of solvolysis involving displacement of chloride from the trivalent phosphorus of chlorodiphenylphosphine (Ph2PCl, 1) are reported for ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, acetone, 2,2,2-trifluoroethanol (TFE), and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The 25 solvents give an extended Grunwald-Winstein correlation with an l value of 1.25 0.09, m value of 0.46 0.06, and correlation coefficient (R) of 0.954. The reactions in aqueous acetone were unusually fast, and these data points lie above the plot. Specific rate values are also reported for TFE-ethanol mixtures. For five representative solvents, values were obtained at three additional temperatures and activation parameters are presented. Rather low enthalpies of activation (8.4 to 11.8 kcal mol-1) are accompanied by very negative entropies of activation (-33 to -46 cal mol-1K-1). The kinetic features observed are consistent with an SN2 reaction incorporating appreciable bond formation and bond breaking at the transition state, and they are very similar to those previously observed for diphenylphosphinyl chloride (Ph2POCl).

METHOD FOR PRODUCING ORGANOPHOSPHORUS COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an organophosphorus compound which has excellent energy efficiency without containing a halogenated alkyl or a by-product derived from a halogenated alkyl. SOLUTION: There is provided a method for producing an organophosphorus compound by reacting a trivalent organophosphorus compound represented by the following general formula (1) in the presence of a super strong acid and/or at least one acid catalyst containing a solid superstrong acid catalyst to generate a pentavalent organophosphorus compound represented by the following general formula. (where Z1 represents OR2 or R2; Z2 represents OR3 or R3; R1, R2 and R3 represent an alkyl group, an alkenyl group or the like; when R2 and R3 are an alkyl group or the like, R2 and R3 may be bonded to each other to form a cyclic structure; and R1 may be a hydrogen atom.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Bipyridine structure ligand and preparation method thereof, bipyridine structure-based catalytic system and application of bipyridine structure-based catalytic system in ethylene oligomerization

The invention provides a bipyridine structure ligand represented by a formula I and a preparation method thereof, and the invention also provides a catalytic system based on the bipyridine structure and an application of the catalytic system in ethylene oligomerization, wherein the catalytic system comprises the bipyridine structure ligand, a metal precursor taking chromium as a center and a cocatalyst. The catalytic system can improve the selectivity of 1-octene and greatly reduce oligomers in ethylene oligomerization reaction, the selectivity of the 1-octene is 79.2%, the content of the oligomer is 0.8%, and possibility is provided for ethylene oligomerization industrialization.

Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds

Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.

Synthesis method of trisubstituted phosphine oxide compound

The invention provides a synthesis method of a trisubstituted phosphine oxide compound. In the method, monohydric alcohol or dihydric alcohol which is inexpensive, readily available, stable and low intoxicity are used as alkylating agents, and cheap and readily available halosilane is used as a catalyst, thus directly obtaining the trisubstituted phosphine oxide compound through high-selectivityreaction. The reaction method is simple, the conditions are mild, no solvent is needed, the operation is easy, and water is a reaction by-product. The method has low requirements on the reaction conditions, and benzyl type, allyl type and aliphatic type alcohol can be used as the alkylating agent to realize the synthesis of the target phosphine oxide compound, and has a relatively wide applicationrange. The method can also conveniently scale up the production by 20 times and carry out the gram-level preparation of products, so the method should also have certain research and industrial application prospects.

Exploring the Reactivity of Donor-Stabilized Phosphenium Cations: Lewis Acid-Catalyzed Reduction of Chlorophosphanes by Silanes

Phosphane-stabilized phosphenium cations react with silanes to effect either reduction to primary or secondary phosphanes, or formation of P-P bonded species depending upon counteranion. This operates for in situ generated phosphenium cations, allowing catalytic reduction of P(III)-Cl bonds in the absence of strong reducing agents. Anion and substituent dependence studies have allowed insight into the competing mechanisms involved.

Direct C-OH/P(O)-H dehydration coupling forming phosphine oxides

A t-BuONa-mediated C-OH/P(O)-H cross dehydration coupling to produce alkylphosphine oxides is developed. This reaction employed readily available alcohols and P(O)-H compounds as the starting materials, providing an efficient alternative method for constructing sp3 C-P bonds. A reasonable reaction path involving dehydration and subsequent regio-selective hydrophosphorylation of the resulting alkenes was proposed.

Outer-Sphere Reactivity Shift of Secondary Phosphine Oxide-Based Nickel Complexes: From Ethylene Hydrophosphinylation to Oligomerization

A new dimension for secondary phosphine oxide (SPOs) ligands is described in this article. Demonstrated on original π-allylic nickel structures, these self-assembled complexes trigger catalytic hydrophosphinylation reactions. Addition of a Lewis acid B(C6F5)3 switches the reactivity towards migratory insertion and thus ethylene oligomerization through an unprecedented outer-sphere interaction with the coordinated SPO ligand. NMR experiments and X-ray analyses allowed for the observation of the formation of zwitterionic active species as well as their degradation pathway.

The Mechanism of Phosphonium Ylide Alcoholysis and Hydrolysis: Concerted Addition of the O?H Bond Across the P=C Bond

The previous work on the hydrolysis and alcoholysis reactions of phosphonium ylides is summarized and reviewed in the context of their currently accepted mechanisms. Several experimental facts relating to ylide hydrolysis and to salt and ylide alcoholysis are shown to conflict with those mechanisms. In particular, we demonstrate that the pKavalues of water and alcohols are too high in organic media to bring about protonation of ylide. Therefore, we propose concerted addition of the water or alcohol O?H bond across the ylide P=C bond. In support of this, we provide NMR spectroscopic evidence for equilibrium between ylide and aclohol that does not require the involvement of phosphonium hydroxide. We report the first P-alkoxyphosphorane to be characterised by NMR spectroscopy that does not undergo exchange on an NMR timescale. Two-dimensional NMR spectroscopic techniques have been applied to the characterisation to P-alkoxyphosphoranes for the first time.