Otera's Catalyst
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Otera's Catalyst
Otera's catalyst, named after Japanese chemist Junzo Otera, is an organostannane compound which has been used as a transesterification catalyst. This isothioscyanate compound is a member of a family of organostannanes reported by Wada and coworkers, and elaborated upon by Otera and coworkers. Preparation This class of compounds may be prepared generally by the reaction of an organotin halide and oxide: : 2 R2SnO + 2 R2SnX2 → (XR2SnOSnR2X)2 In particular, the thiocyanate compound was prepared by the reaction of dibutyltin oxide with dibutyltin diisothiocyanate. Otherwise, this compound is not commercially available. Applications This thiocyanate compound can be used as a transesterification catalyst. Although it is not well known, it has been used in a number of total syntheses. In this application, the reaction occurs via the displacement of the bridging isothiocyanate ligands with the incoming alcohol to form an alcohol-bridged active catalyst. Tin acts as the Lewis acid, and ...
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Organostannane Compound
Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory. Structure Organotin compounds are generally classified according to their oxidation states. Tin(IV) compounds are much more common and more useful. Organic derivatives of tin(IV) The tetraorgano derivatives are invariably tetrahedral. Compounds of the type SnRR'R''R have been resolved into individual enantiomers. Organotin halides Organotin chlorides have the formula for values of ''n'' up to 3. Bromides, iodides, and fluorides are also known but less important. These ...
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Transesterification
In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction can also be accomplished with the help of other enzymes, particularly lipases (one example is the lipase E.C.3.1.1.3). Strong acids catalyse the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile, whereas bases catalyse the reaction by removing a proton from the alcohol, thus making it more nucleophilic. If the alcohol produced by the reaction can be separated from the reactants by distillation this will drive the equilibrium toward the products, this means that esters with larger alkoxy groups can be made from methyl or ethyl esters in high purity by heating the mixture of ester, acid/base, and large alcohol. Mechanism In the transesterification mechanism, the carbonyl carbon of the starting e ...
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Chem
Chem may refer to: * Chemistry practical waali mam *Chemistry *Chemical * ''Chem'' (journal), a scientific journal published by Cell Press *Post apocalyptic slang for "drugs", medicinal or otherwise in the Fallout video game series. In Ancient Egyptian usage: * ''Khem'' (also spelt ''Chem''), the Egyptian word for "black" * Min (god), in the past erroneously named ''Khem'' CHEM may refer to : *A metabolic panel: for instance, CHEM-7, which is the basic metabolic panel *CHEM-DT CHEM-DT is the TVA owned-and-operated television station in Trois-Rivières, Quebec, Canada. It broadcasts a high-definition digital signal on VHF channel 8 from a transmitter on Rue Principale in Notre-Dame-du-Mont-Carmel. Owned by the Grou ..., a Canadian television channel See also * Chemo (other) * Kemi, a place in Finland {{disambig ...
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Catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in 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. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usually gaseous or liquid) as the reactant, or heterogeneous, whose components are not in the same phase. Enzymes and other biocatalysts are often considered as a third category. Catalysis is ubiquitous in chemical industry of all kinds. Estimates are that 90% of all commercially produced chemical products involve catalysts at some s ...
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Lewis Acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane (Me3B) is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as po ...
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Organotin Compounds
Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory. Structure Organotin compounds are generally classified according to their oxidation states. Tin(IV) compounds are much more common and more useful. Organic derivatives of tin(IV) The tetraorgano derivatives are invariably tetrahedral. Compounds of the type SnRR'R''R have been resolved into individual enantiomers. Organotin halides Organotin chlorides have the formula for values of ''n'' up to 3. Bromides, iodides, and fluorides are also known but less important. These ...
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Catalysts
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in 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. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usually gaseous or liquid) as the reactant, or heterogeneous, whose components are not in the same phase. Enzymes and other biocatalysts are often considered as a third category. Catalysis is ubiquitous in chemical industry of all kinds. Estimates are that 90% of all commercially produced chemical products involve catalysts at some sta ...
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Thiocyanates
Thiocyanate (also known as rhodanide) is the anion . It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Mercury(II) thiocyanate was formerly used in pyrotechnics. Thiocyanate is analogous to the cyanate ion, , wherein oxygen is replaced by sulfur. is one of the pseudohalides, due to the similarity of its reactions to that of halide ions. Thiocyanate used to be known as rhodanide (from a Greek word for rose) because of the red colour of its complexes with iron. Thiocyanate is produced by the reaction of elemental sulfur or thiosulfate with cyanide: : 8 CN- + S8 -> 8 SCN- : CN- + S2O3^2- -> SCN- + SO3^2- The second reaction is catalyzed by thiosulfate sulfurtransferase, a hepatic mitochondrial enzyme, and by other sulfur transferases, which together are responsible for around 80% of cyanide metabolism in the body. Biological chemistry of thiocyanate in medicine Thiocyanate is known to be ...
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