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Hydrofunctionalization
A hydrofunctionalization reaction is the addition of hydrogen and another univalent fragment (X) across a carbon-carbon or carbon-heteroatom multiple bond. Often, the term ''hydrofunctionalization'' without modifier refers specifically to the use of the covalent hydride (H-X) as the source of hydrogen and X for this transformation. If other reagents are used to achieve the net addition of hydrogen and X across a multiple bond, the process may be referred to as a ''formal hydrofunctionalization''. For terminal olefins (or acetylenes), the regioselectivity of the process can be described as Markovnikov (addition of X at the substituted end) or anti-Markovnikov (addition of X at the unsubstituted end). Catalysts are frequently employed to control the chemo-, regio-, and stereoselectivity of hydrofunctionalization reactions. Examples Some of the better known classes of hydrofunctionalization reactions include the following: *Hydroboration *Hydrosilylation *Hydrometalation (incl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroalkoxylation
Hydroalkoxylation is a chemical reaction that combines alcohols with alkenes or alkynes. The process affords ethers. The reaction converts alkenes to dialkyl or aryl-alkyl ethers: :R'OH + RCH=CH2 → R'OCH(R)-CH3 Similarly, alkynes are converted to vinyl ethers: :R'OH + RC≡CH → R'OC(R)=CH2 As shown, the reaction follows the Markovnikov rule. The process exhibits good atom-economy in the sense that no byproducts are produced. The reaction is catalyzed by bases and also by transition metal complexes. Usually symmetrical ethers are prepared by dehydration of alcohols and unsymmetrical ethers by the Williamson ether synthesis from alkyl halides and alkali metal alkoxides.Wilhelm Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" ''Ullmann's Encyclopedia of Industrial Chemistry'' 2002, Wiley-VCH, Weinheim. {{doi, 10.1002/14356007.a10_023 See also * Hydroamination * Hydrofunctionalization A hydrofunctionalization reaction is the addition of hydrogen and another univalen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroamination
In organic chemistry, hydroamination is the addition of an bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene. In the ideal case, hydroamination is atom economical and green. Amines are common in fine-chemical, pharmaceutical, and agricultural industries. Hydroamination can be used intramolecularly to create heterocycles or intermolecularly with a separate amine and unsaturated compound. The development of catalysts for hydroamination remains an active area, especially for alkenes. Although practical hydroamination reactions can be effected for dienes and electrophilic alkenes, the term hydroamination often implies reactions metal-catalyzed processes. History Hydroamination is well-established technology for generating fragrances from myrcene. In this conversion, diethylamine adds across the diene substituent, the reaction being catalyzed by lithium diethylamide. Intramolecular hydroaminations were reported by Tobin J. Marks in 1989 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Generic Hydrofunctionalization Reaction
Generic or generics may refer to: In business * Generic term, a common name used for a range or class of similar things not protected by trademark * Generic brand, a brand for a product that does not have an associated brand or trademark, other than the trading name of the business providing the product * Generic trademark, a trademark that sometimes or usually replaces a common term in colloquial usage * Generic drug, a drug identified by its chemical name rather than its brand name In computer programming * Generic function, a computer programming entity made up of all methods having the same name * Generic programming, a computer programming paradigm based on method/functions or classes defined irrespective of the concrete data types used upon instantiation ** Generics in Java In linguistics *A pronoun or other word used with a less specific meaning, such as: ** generic ''you'' ** generic ''he'' or generic ''she'' ** generic ''they'' * Generic mood, a grammatical mood used ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroboration
In organic chemistry, hydroboration refers to the addition of a hydrogen-boron bond to certain double and triple bonds involving carbon (, , , and ). This chemical reaction is useful in the organic synthesis of organic compounds. Hydroboration produces organoborane compounds that react with a variety of reagents to produce useful compounds, such as alcohols, amines, or alkyl halides. The most widely known reaction of the organoboranes is oxidation to produce alcohols typically by hydrogen peroxide. This type of reaction has promoted research on hydroboration because of its mild condition and a wide scope of tolerated alkenes. Another research subtheme is metal-catalysed hydroboration. The development of this technology and the underlying concepts were recognized by the Nobel Prize in Chemistry to Herbert C. Brown. He shared the prize with Georg Wittig in 1979 for his pioneering research on organoboranes as important synthetic intermediates. Addition of a H-B bond to C-C doubl ... [...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] |
Hydrometalation
Hydrometalation (hydrometallation) is a type of chemical reaction in organometallic chemistry in which a chemical compound with a hydrogen to metal bond (M-H, metal hydride) adds to compounds with an unsaturated bond like an alkene (RC=CR) forming a new compound with a carbon to metal bond (RHC-CRM).Elschenbroich, C. ”Organometallics” (2006) Wiley-VCH: Weinheim. The metal is less electronegative than hydrogen, the reverse reaction is beta-hydride elimination. The reaction is structurally related to carbometalation. When the substrate is an alkyne the reaction product is a vinylorganometallic. : Examples are hydroboration, hydroalumination, 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 ... and hydrozirconation. References {{Reflist Organometallic chemistry ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydration Reaction
In chemistry, a hydration reaction is a chemical reaction A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ... in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.. Organic chemistry Epoxides to glycol Several million tons of ethylene glycol are produced annually by the hydration of oxirane, a cyclic compound also known as ethylene oxide: : C2H4O + H2O → HO–CH2CH2–OH Acid catalysts are typically used. Alkenes For the hydration of alkenes, the general chemical equation of the reaction is the following: :RRC=CH2 + H2O → RRC(OH)-CH3 A hydroxyl group (OH−) attaches to one carbon of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrohalogenation
A hydrohalogenation reaction is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes. : If the two carbon atoms at the double bond are linked to a different number of hydrogen atoms, the halogen is found preferentially at the carbon with fewer hydrogen substituents, an observation known as Markovnikov's rule. This is due to the abstraction of a hydrogen atom by the alkene from the acid (HX) to form the most stable carbocation (relative stability: 3°>2°>1°>methyl), as well as generating a halogen anion. A simple example of a hydrochlorination is that of indene with hydrogen chloride gas (no solvent): : Alkynes also undergo hydrohalogenation reactions. Depending on the exact substrate, alkyne hydrohalogenation can proceed though a concerted protonation/nucleophilic attack (AdE3) or stepwise by first protonating the alkyne to form a vinyl cation, followed by attack of HX/X− to give the produc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrovinylation
In organic chemistry, hydrovinylation is the formal insertion of an alkene into the C-H bond of ethylene (). The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reaction is catalyzed by metal complexes. A representative reaction is the conversion of styrene and ethylene to 3-phenybutene: :\ce + \longrightarrow \ce Ethylene dimerization The dimerization of ethylene gives 1-butene is another example of a hydrovinylation. In the Dimersol and Alphabutol Processes, alkenes are dimerized for the production of gasoline and for comonomers such as 1-butene. These processes operate at several refineries across the world at the scales of about 400,000 tons/year (2006 report). 1-Butene is amenable to isomerization to 2-butenes, which is used in Olefin conversion technology to give propylene. Hydroarylation Hydroarylation is again a special case of hydrovinylation. Hydroarylation has been demonstrated for alk ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroacylation
Hydroacylation is a type of organic reaction in which an alkene is inserted into the a formyl C-H bond. The product is a ketone. The reaction requires a metal catalyst. It is almost invariably practiced as an intramolecular reaction using homogeneous catalysts, often based on rhodium phosphines. :RCHO + CH2=CHR' → RC(O)CH2CH2R' With an alkyne in place of alkenes, the reaction produce an α,β-unsaturated ketone. Examples The reaction was discovered as part of a synthetic route to certain prostanoids. The reaction required tin tetrachloride and a stoichiometric amount of Wilkinson's catalyst. An equal amount of a cyclopropane was formed as the result of decarbonylation. : The first catalytic application involved cyclization of 4-pentenal to cyclopentanone using with Wilkinson's catalyst. In this reaction the solvent was saturated with ethylene. :CH2=CHCH2CH2CHO → (CH2)4CO Reaction mechanism Labeling studies establish the following regiochemistry: :RCDO + CH2=CHR' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon double bond. This process has undergone continuous growth since its invention: Production capacity reached 6.6×106 tons in 1995. It is important because aldehydes are easily converted into many secondary products. For example, the resulting aldehydes are hydrogenated to alcohols that are converted to detergents. Hydroformylation is also used in speciality chemicals, relevant to the organic synthesis of fragrances and drugs. The development of hydroformylation is one of the premier achievements of 20th-century industrial chemistry. The process entails treatment of an alkene typically with high pressures (between 10 and 100 atmospheres) of carbon monoxide and hydrogen at temperatures between 40 and 200 °C. In one variation, formaldehyd ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
