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Potassium Tert-butoxide
Potassium ''tert''-butoxide (or potassium ''t''-butoxide) is a chemical compound with the formula CH3)3COKsub>''n'' (abbr. KOtBu). This colourless solid is a strong base (pKa of conjugate acid is 17 in H2O), which is useful in organic synthesis. The compound is often depicted as a salt, and it often behaves as such, but its ionization depends on the solvent. Preparation Potassium ''t''-butoxide is commercially available as a solution and as a solid, but it is often generated ''in situ'' for laboratory use because samples are so moisture- sensitive and older samples are often of low purity. It is prepared by the reaction of dry ''tert''-butyl alcohol with potassium metal. The solid is obtained by evaporating these solutions followed by heating the solid. The solid can be purified by sublimation. Structure It crystallizes as a tetrameric cubane-type cluster. It crystallises from tetrahydrofuran/pentane at −20 °C as BuOK·tBuOHsub>∞, which consists of straig ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken or new bonds formed or both. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, usin ...
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Hexamethylphosphoramide
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is used as a solvent in organic synthesis. Structure and reactivity HMPA is the oxide of tris(dimethylamino)phosphine, P(NMe2)3. Like other phosphine oxides (such as triphenylphosphine oxide), the molecule has a tetrahedral core and a P=O bond that is highly polarized, with significant negative charge residing on the oxygen atom. Compounds containing a nitrogen–phosphorus bond typically are degraded by hydrochloric acid to form a protonated amine and phosphate. It dissolves alkali metal salts and alkali metals, forming blue solutions which are stable for a few hours. Solvated electrons are present in these blue solutions. Applications HMPA is a specialty solvent for polymers, gases, and organometallic compounds. It improves the selectivity of lithiation reactions by breaking up the oligomers of lithium bases such as butyllithium. ...
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Dichloromethane
Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.Rossberg, M. ''et al.'' (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. . Occurrence Natural sources of dichloromethane include oceanic sources, macroalgae, wetlands, and volcanoes. However, the majority of dichloromethane in the environment is the result of industrial emissions. Production DCM is produced by treating either chloromethane or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and chloromethane undergo a series of reactions producing progressively more chlorinated products. In this way, an estimated 400,000 tons were produced in the US, Europe, and Japan in 199 ...
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Robert H
The name Robert is an ancient Germanic given name, from Proto-Germanic "fame" and "bright" (''Hrōþiberhtaz''). Compare Old Dutch ''Robrecht'' and Old High German ''Hrodebert'' (a compound of ''Hrōþ, Hruod'' () "fame, glory, honour, praise, renown, godlike" and ''berht'' "bright, light, shining"). It is the second most frequently used given name of ancient Germanic origin.Reaney & Wilson, 1997. ''Dictionary of English Surnames''. Oxford University Press. It is also in use Robert (surname), as a surname. Another commonly used form of the name is Rupert (name), Rupert. After becoming widely used in Continental Europe, the name entered England in its Old French form ''Robert'', where an Old English cognate form (''Hrēodbēorht'', ''Hrodberht'', ''Hrēodbēorð'', ''Hrœdbœrð'', ''Hrœdberð'', ''Hrōðberχtŕ'') had existed before the Norman Conquest. The feminine version is Roberta (given name), Roberta. The Italian, Portuguese, and Spanish form is Roberto (given name), ...
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Brian Stoltz
Brian M. Stoltz is currently a professor of chemistry at the California Institute of Technology. The primary focus of his research is chemical synthesis with an emphasis on expanding the scope of allylic alkylation for the preparation of complex molecules possessing unique structural, biological, and physical properties. His research involves the total synthesis of natural products such as dragmacidin F and (–)-cyanthiwigin F, and development of synthetic reactions to access quaternary stereocenters. Specifically, he has focused on the Tsuji–Trost reaction, allylic alkylation of enolates, developing an Enantioselective synthesis, enantioselective variant in 2004. Education Stoltz received undergraduate degrees in Chemistry and German from Indiana University of Pennsylvania in 1993. As an undergraduate he spent a year abroad at the Ludwig Maximilian University of Munich. He went on to earn his M.S. and Ph.D. at Yale University, where he studied organic chemistry under the su ...
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Silanes
In organosilicon chemistry, silanes are a diverse class of charge-neutral organic compounds with the general formula . The R substituents can be any combination of organic or inorganic groups. Most silanes contain Si-C bonds, and are discussed under organosilicon compounds. Some contain Si-H bonds and are discussed under hydrosilanes. Examples *Silane , the parent. * Binary silicon-hydrogen compounds (which are sometimes called silanes also) includes silane itself but also compounds with Si-Si bonds including disilane and longer chains. *Silanes with one, two, three, or four Si-H bonds are called hydrosilanes. Silane is again the parent member. Examples: triethylsilane () and triethoxysilane (). * Polysilanes are organosilicon compounds with the formula . They feature Si-Si bonds. Attracting more interest are the organic derivatives such as polydimethylsilane . Dodecamethylcyclohexasilane is an oligomer of such materials. Formally speaking, polysilanes also include co ...
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Catalysis
Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst. The rate increase occurs because the catalyst allows the reaction to occur by an alternative mechanism which may be much faster than the noncatalyzed mechanism. However the noncatalyzed mechanism does remain possible, so that the total rate (catalyzed plus noncatalyzed) can only increase in the presence of the catalyst and never decrease. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usual ...
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Elimination Reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1cB-elimination reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism, Ei mechanism. E2 mechanism The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which ''carbon-hydrogen'' and ''carbon-halogen'' bonds break to form a double bond (''C=C molecular geometry, Pi bond''). The specifics of the re ...
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Cyclopropanation
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () Ring (chemistry), rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly Reactivity (chemistry), reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic reaction, cheletropic manner. Approaches From alkenes using carbenoid reagents Several methods exist for converting alkenes to cyclopropane rings using carbene type reagents. As carbenes themselves are highly reactive it is common for them to be used in a stabilised form, referred to as a carbenoid. Simmons–Smith reaction In the Simmons–Smith reaction the reactive carbenoid is iodomethylzinc iodide, ...
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Dichlorocarbene
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds. Preparation Dichlorocarbene is most commonly generated by reaction of chloroform and a base such as potassium tert-butoxide, potassium ''tert''-butoxide or aqueous sodium hydroxide. A phase transfer catalyst, for instance quaternary ammonium cation, benzyltriethylammonium bromide, facilitates the migration of the hydroxide in the organic phase. :HCCl3 + NaOH → CCl2 + NaCl + H2O Other reagents and routes Another precursor to dichlorocarbene is ethyl trichloroacetate. Upon treatment with sodium methoxide it releases CCl2. Phenyl(trichloromethyl)mercury decomposes thermally to release CCl2. :PhHgCCl3 → CCl2 + PhHgCl Dichlorodiazirine, which is stable in the dark, chemical decomposition, decomposes into dic ...
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Dehydrohalogenation
In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate (chemistry), substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halides Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol#Hydrolysis of chlorobenzene, phenol via a benzyne intermediate. Base-promoted reactions to alkenes When treated with a strong base many alkyl chlorides convert to corresponding alkene. It is also called a β-elimination reaction and is a type of elimination reaction. Some prototypes are shown below: :\begin \ce\ &\ce \\ \ce\ &\ce \\ \ce\ &\ce \end Here ethyl chloride reacts with potassium hydroxide, ty ...
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Active Methylene Compound
In chemistry, a methylene bridge is part of a molecule with formula . The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene bridge is often called a methylene group or simply methylene, as in "methylene chloride" (dichloromethane ). As a bridge in other compounds, for example in cyclic compounds, it is given the name methano. However, the term methylidene group (not to be confused with the term methylene group, nor the carbene methylidene) properly applies to the group when it is connected to the rest of the molecule by a double bond (), giving it chemical properties very distinct from those of a bridging group. Organic chemistry It is the repeating unit in the skeleton of the unbranched alkanes. Polyethylene also can be called polymethylene. Compounds possessing a methylene bridge located between two electron withdrawing groups (such as nitro, carbonyl or nitrile groups) are sometimes called active methylene co ...
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