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Diphenylphosphine Oxide
Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents. Synthesis Diphenylphosphine oxide can be prepared by the reaction of phosphonic esters, such as diethylphosphite, with Grignard reagents followed by acid workup: :(C2H5O)2P(O)H + 3C6H5MgBr → (C6H5)2P(O)MgBr + C2H5OMgBr :(C6H5)2P(O)MgBr + HCl → (C6H5)2P(O)H + MgBrCl Alternatively, it may be prepared by the partial hydrolysis of chlorodiphenylphosphine or diphenylphosphine. Reactions Diphenylphosphine oxide exists in equilibrium with its minor tautomer diphenylphosphinous acid, ((C6H5)2POH: : Diphenylphosphine oxide is used in Buchwald-Hartwig coupling reactions to introduce diphenylphosphino substituents. Thionyl chloride converts diphenylphosphine oxide to chlorodiphenylphosphine. Organophosphinous acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligand A metal-phos ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organophosphorus Compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds. Phosphorus can adopt ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethylphosphite
Diethylphosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethylphosphite is a colorless liquid. The molecule is tetrahedral. Synthesis and properties The compound was probably prepared in the 1850s by combining phosphorus trichloride and ethanol, but intentional preparations came later. It arises as follows: :PCl3 + 3 C2H5OH → (C2H5O)2P(O)H + 2 HCl + C2H5Cl Many derivatives can be prepared similarly. Despite being named as a phosphite it exists overwhelmingly in its phosphonate form, , a property it shares with its parent acid phosphorous acid; despite this many of its reactions are difficult to rationalise without assuming the existence of the following tautomerism equilibrium between phosphorus(V) and phosphorus(III) forms: :(C2H5O)2PV(O)H ⇌ (C2H5O)2PIII(OH) Reactions Alkoxide exchange Diethylphosphite undergoes transesterific ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grignard Reagent
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used. In this aspect, they are similar to organolithium reagents. Pure Grignard reagents are extremely reactive solids. They are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran; which are relatively stable as long as water is excluded. In such a medium, a Grignard reagent is invariably present as a complex with the magnesium atom conn ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chlorodiphenylphosphine
Chlorodiphenylphosphine is an organophosphorus compound with the formula (C6H5)2PCl, abbreviated Ph2PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is useful reagent for introducing the Ph2P group into molecules, which includes many ligands.Quin, L. D. ''A Guide to Organophosphorus Chemistry''; Wiley IEEE: New York, 2000; pp 44-69. Like other halophosphines, Ph2PCl is reactive with many nucleophiles such as water and easily oxidized even by air. Synthesis and reactions Chlorodiphenylphosphine is produced on a commercial scale from benzene and phosphorus trichloride (PCl3). Benzene reacts with phosphorus trichloride at extreme temperatures around 600 °C to give dichlorophenylphosphine (PhPCl2) and HCl. Redistribution of PhPCl2 in the gas phase at high temperatures results in chlorodiphenylphosphine. :2PhPCl2 → Ph2PCl + PCl3 Alternatively such compounds are prepared by redistribu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diphenylphosphine
Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (C6H5)2PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts. Synthesis Diphenylphosphine can be prepared from triphenylphosphine by reduction to lithium diphenylphosphide, which can be protonated to give the title compound: :PPh3 + 2 Li → LiPPh2 + LiPh :LiPPh2 + H2O → Ph2PH + LiOH Uses and reactions In the laboratory, diphenylphosphine is a common intermediate. It can be deprotonated to give diphenylphosphide derivatives: :Ph2PH + nBuLi → Ph2PLi + nBuH The preparation of phosphine ligands, Wittig-Horner reagents, and phosphonium salts are commonly accomplished by alkylating diphenylphosphine. The hydrogen atom connected to phosphorus undergoes Michael-like addition to activated alkenes, providing products with which to produce phosphine ligands such as 1,2-bis(diphenylphosphino)ethane 1,2-Bi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphinous Acid
Phosphinous acid is the inorganic compound with the formula H2POH. It exists, fleetingly, as a mixture with its less stable tautomer H3PO (phosphine oxide). This mixture has been generated by low temperature oxidation of phosphine with ozone. H2POH is mainly of pedagogical interest. Organophosphinous acids are more prevalent than the parent H2POH. Organophosphinous acids Phosphinous acids exist mainly as minor tautomers of secondary phosphine oxides. For example diphenylphosphinous acid, which is not detectable directly, is invoked as the tautomer of diphenylphosphine oxide Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents. Synthesis Diphenylphosphine oxide can be prepared by the reaction of phosphonic esters, such as d .... Highly electron-withdrawing substituents stabilize the phosphinous acid tautomer as illustrated by (CF3)2POH.{{cite journal , doi=10.1002/chem.201102370, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
DIBAH
Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the chemical formula, formula (''i''-Bu2AlH)2, where ''i''-Bu represents isobutyl (-CH2CH(CH3)2). This Organoaluminum, organoaluminium compound is a reagent in organic synthesis. Properties Like most organoaluminum compounds, the compound's structure is most probably more than that suggested by its empirical formula. A variety of techniques, not including X-ray crystallography, suggest that the compound exists as a Dimer (chemistry), dimer and a trimer, consisting of tetrahedral aluminium centers sharing bridging hydride ligands. Hydrides are small and, for aluminium derivatives, are highly base (chemistry), basic, thus they bridge in preference to the alkyl groups. DIBAL can be prepared by heating triisobutylaluminium (itself a dimer) to induce beta-hydride elimination: :(''i''-Bu3Al)2 → (''i''-Bu2AlH)2 + 2 isobutene, (CH3)2C=CH2 Although DIBAL can be purchased commercially as a colorless li ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphine Ligand
A metal-phosphine complex is a In coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. Prominent examples of metal phosphine complexes include Wilkinson's catalyst (Rh(PPh3)3Cl), Grubbs' catalyst, and tetrakis(triphenylphosphine)palladium(0). Preparation Many metal phosphine complexes are prepared by reactions of metal halides with preformed phosphines. For example, treatment of a suspension of palladium chloride in ethanol with triphenylphosphine yields monomeric bis(triphenylphosphine)palladium(II) chloride units. : dCl2sub>n + 2PPh3 → PdCl2(PPh3)2 The first reported phosphine complexes were ''cis''- and ''trans''-PtCl2(PEt3)2 reported by Cahours and Gal in 1870. Often the phosphine serves both as a ligand and as a reductant. This property is illustrated by the synthesis of many platinum-metal complexes of triphenylph ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organophosphine Oxides
Organophosphines are organophosphorus compounds with the formula PR''n''H3−''n'', where R is an organic substituent. These compounds can be classified according to the value of ''n'': primary phosphines (''n'' = 1), secondary phosphines (''n'' = 2), tertiary phosphines (''n'' = 3). All adopt pyramidal structures. Organophosphines are generally colorless, lipophilic liquids or solids. The parent of the organophosphines is phosphine (PH3). Annette Schier and Hubert Schmidbaur"P-Donor Ligands" in Encyclopedia of Inorganic Chemistry 2006, Wiley-VCH, Weinheim. 1° vs 2° vs 3° phosphines Organophophines are classified according to the number of organic substituents. Primary phosphines Primary (1°) phosphines, with the formula RPH2, are typically prepared by alkylation of phosphine. Simple alkyl derivatives such as methylphosphine (CH3PH2) are prepared by alkylation of alkali metal derivatives MPH2 (M is Li, Na, or K). Another synthetic route in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
