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Tris(pentafluorophenyl)borane
Tris(pentafluorophenyl)borane, sometimes referred to as "BCF", is the chemical compound . It is a white, volatile solid. The molecule consists of three pentafluorophenyl groups attached in a "paddle-wheel" manner to a central boron atom; the core is planar. It has been described as the “ideal Lewis acid” because of its high thermal stability and the relative inertness of the B-C bonds. Related fluoro-substituted boron compounds, such as those containing groups, decompose with formation of B-F bonds. Tris(pentafluorophenyl)borane is thermally stable at temperatures well over 200 °C, resistant to oxygen, and water-tolerant. Preparation Tris(pentafluorophenyl)borane is prepared using a Grignard reagent derived from bromopentafluorobenzene: : The synthesis originally employed , but this reagent can detonate with elimination of . Structure The structure of tris(pentafluorophenyl)borane (BCF) was determined by gas electron diffraction. It has a propeller-like arrangement o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Frustrated Lewis Pair
A frustrated Lewis pair (FLP) is a compound or mixture containing a Lewis acid and a Lewis base that, because of steric hindrance, cannot combine to form a classical adduct. Many kinds of FLPs have been devised, and many simple substrates exhibit activation. The discovery that some FLPs split H2 triggered a rapid growth of research into FLPs. Because of their "unquenched" reactivity, such systems are reactive toward substrates that can undergo heterolysis. For example, many FLPs split hydrogen molecules. Thus, a mixture of tricyclohexylphosphine (PCy3) and tris(pentafluorophenyl)borane reacts with hydrogen to give the respective phosphonium and borate ions: :PCy3 + B(C6F5)3 + H2 -> PCy3 B(C6F5)3 This reactivity has been exploited to produce FLPs which catalyse hydrogenation reactions. Small molecule activation Frustrated Lewis pairs have been shown to activate many small molecules, either by inducing heterolysis or by coordination. Hydrogen The discovery that some ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Noncoordinating Anion
Anions that interact weakly with cations are termed non-coordinating anions, although a more accurate term is weakly coordinating anion. Non-coordinating anions are useful in studying the reactivity of electrophilic cations. They are commonly found as counterions for cationic metal complexes with an unsaturated coordination sphere. These special anions are essential components of homogeneous alkene polymerisation catalysts, where the active catalyst is a coordinatively unsaturated, cationic transition metal complex. For example, they are employed as counterions for the 14 valence electron cations C5H5)2ZrRsup>+ (R = methyl or a growing polyethylene chain). Complexes derived from non-coordinating anions have been used to catalyze hydrogenation, hydrosilylation, oligomerization, and the living polymerization of alkenes. The popularization of non-coordinating anions has contributed to increased understanding of agostic complexes wherein hydrocarbons and hydrogen serve as ligands. N ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bromopentafluorobenzene
Bromopentafluorobenzene is an organofluorine compound with the formula C6F5Br. It is a colorless liquid that is used to prepare pentafluophenyl compounds. These syntheses typically proceed via the intermediacy of C6F5Li or the Grignard reagent. Illustrative is preparation of tris(pentafluorophenyl)borane Tris(pentafluorophenyl)borane, sometimes referred to as "BCF", is the chemical compound . It is a white, volatile solid. The molecule consists of three pentafluorophenyl groups attached in a "paddle-wheel" manner to a central boron atom; the c ...: :3 C6F5MgBr + BCl3 → (C6F5)3B + 3 MgBrCl Other derivatives include LiB(C6F5)4, uC6F5sub>4, and Ni(C6F5)2(dioxane)2.{{cite journal, authors=Sanchez, G.; Momblona, F.; Sanchez, M.; Perez, J.; Lopez, G.; Casabo, J.; Molins, E.; Miravitlles, C., title=Synthesis of Homo- and Heterobimetallic Complexes Containing the Ni(C6F5)2 Moiety. Crystal Structure of C6F5)2Ni(μ-SPh)2Pd(dppe)journal=Eur. J. Inorg. Chem. , year=1998, vo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylborane
Triphenylborane, often abbreviated to BPh3 where Ph is the phenyl group C6H5-, is a chemical compound with the formula B(C6H5)3. It is a white crystalline solid and is both air and moisture sensitive, slowly forming benzene and triphenylboroxine. It is soluble in aromatic solvents. Structure and properties The core of the compound, BC3, has a trigonal planar structure. The phenyl groups are rotated at about a 30° angle from the core plane. Even though triphenylborane and tris(pentafluorophenyl)borane are structurally similar, their Lewis acidity is not. BPh3 is a weak Lewis acid while B(C6F5)3 is a strong Lewis acid due to the electronegativity of the fluorine atoms. Other boron Lewis acids include BF3 and BCl3. Synthesis Triphenylborane was first synthesized in 1922. It is typically made with boron trifluoride diethyl etherate and the Grignard reagent, phenylmagnesium bromide. : BF3•O(C2H5)2 + 3 C6H5MgBr → B(C6H5)3 + 3 MgBrF + (C2H5)2O Triphenylborane can al ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylborane
Triphenylborane, often abbreviated to BPh3 where Ph is the phenyl group C6H5-, is a chemical compound with the formula B(C6H5)3. It is a white crystalline solid and is both air and moisture sensitive, slowly forming benzene and triphenylboroxine. It is soluble in aromatic solvents. Structure and properties The core of the compound, BC3, has a trigonal planar structure. The phenyl groups are rotated at about a 30° angle from the core plane. Even though triphenylborane and tris(pentafluorophenyl)borane are structurally similar, their Lewis acidity is not. BPh3 is a weak Lewis acid while B(C6F5)3 is a strong Lewis acid due to the electronegativity of the fluorine atoms. Other boron Lewis acids include BF3 and BCl3. Synthesis Triphenylborane was first synthesized in 1922. It is typically made with boron trifluoride diethyl etherate and the Grignard reagent, phenylmagnesium bromide. : BF3•O(C2H5)2 + 3 C6H5MgBr → B(C6H5)3 + 3 MgBrF + (C2H5)2O Triphenylborane can al ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkenes
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organoboranes
Organoborane or organoboron compounds are chemical compounds of boron and carbon that are organic derivatives of BH3, for example trialkyl boranes. Organoboron chemistry or organoborane chemistry is the chemistry of these compounds. Organoboron compounds are important reagents in organic chemistry enabling many chemical transformations, the most important one called hydroboration. Reactions of organoborates and boranes involve the transfer of a nucleophilic group attached to boron to an electrophilic center either inter- or intramolecularly. α,β-Unsaturated borates, as well as borates with a leaving group at the α position, are highly susceptible to intramolecular 1,2-migration of a group from boron to the electrophilic α position. Oxidation or protonolysis of the resulting organoboranes may generate a variety of organic products, including alcohols, carbonyl compounds, alkenes, and halides. Properties of the B-C bond The C-B bond has low polarity (the difference in electron ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mesityl
Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds. Preparation Mesitylene is prepared by transalkylation of xylene over solid acid catalyst:Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. . :2 C6H4(CH3)2 ⇌ C6H3(CH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Tetrakis(pentafluorophenyl)borate
Lithium tetrakis(pentafluorophenyl)borate is the lithium salt of the weakly coordinating anion (B(C6F5)4)−. Because of its weakly coordinating abilities, lithium tetrakis(pentafluorophenyl)borate makes it commercially valuable in the salt form in the catalyst composition for olefin polymerization reactions and in electrochemistry. It is a water-soluble compound. Its anion is closely related to the non-coordinating anion known as BARF. The tetrakis(pentafluorophenyl)borates have the advantage of operating on a one-to-one stoichiometric basis with Group IV transition metal polyolefin catalysts, unlike methylaluminoxane (MAO) which may be used in large excess. Structure and properties The anion is tetrahedral with B-C bond lengths of approximately 1.65 Angstroms. The salt has only been obtained as the etherate, and the crystallography confirms that four ether (OEt2) molecules are bound to the lithium cation, with Li-O bond lengths of approximately 1.95 Å. The i(OEt2)4sup>+ comp ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tricyclohexylphosphine
Tricyclohexylphosphine is the tertiary phosphine with the formula P( C6H11)3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy3, where Cy stands for cyclohexyl. It is characterized by both high basicity (p''K''a = 9.7) and a large ligand cone angle (170°).{{cite journal , last1 = Immirzi , first1 = A. , last2 = Musco , first2 = A. , title = A Method to Measure the Size of Phosphorus Ligands in Coordination Complexes , doi = 10.1016/S0020-1693(00)95635-4 , year = 1977 , journal = Inorg. Chim. Acta , volume = 25 , pages = L41–42 Important complexes containing P(Cy)3 ligands include the 2005 Nobel Prize-winning Grubbs' catalyst and the homogeneous hydrogenation catalyst Crabtree's catalyst Crabtree's catalyst is an organoiridium compound with the formula ,5-Cyclooctadiene, C8H12IrTricyclohexylphosphine, P(C6H11)3pyridine, C5H5NF6. It is a homogeneous catalyst for hydrogenation and hydrogen-transfer reactions, developed by Rober ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrosilylation
Hydrosilylation, also called catalytic hydrosilation, describes the addition of Si-H bonds across unsaturated bonds."Hydrosilylation A Comprehensive Review on Recent Advances" B. Marciniec (ed.), Advances in Silicon Science, Springer Science, 2009. Ordinarily the reaction is conducted catalytically and usually the substrates are unsaturated organic compounds. Alkenes and alkynes give alkyl and vinyl silanes; aldehydes and ketones give silyl ethers. Hydrosilylation has been called the "most important application of platinum in homogeneous catalysis." Scope and mechanism Hydrosilylation of alkenes represents a commercially important method for preparing organosilicon compounds. The process is mechanistically similar to the hydrogenation of alkenes. In fact, similar catalysts are sometimes employed for the two catalytic processes. The prevalent mechanism, called the Chalk-Harrod mechanism, assumes an intermediate metal complex that contains a hydride, a silyl ligand (R3Si), and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Silica
Silicon dioxide, also known as silica, is an oxide of silicon with the chemical formula , most commonly found in nature as quartz and in various living organisms. In many parts of the world, silica is the major constituent of sand. Silica is one of the most complex and most abundant families of materials, existing as a compound of several minerals and as a synthetic product. Notable examples include fused quartz, fumed silica, silica gel, opal and aerogels. It is used in structural materials, microelectronics (as an Insulator (electricity), electrical insulator), and as components in the food and pharmaceutical industries. Structure In the majority of silicates, the silicon atom shows tetrahedral coordination geometry, tetrahedral coordination, with four oxygen atoms surrounding a central Si atomsee 3-D Unit Cell. Thus, SiO2 forms 3-dimensional network solids in which each silicon atom is covalently bonded in a tetrahedral manner to 4 oxygen atoms. In contrast, CO2 is a linear ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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