Organotin Compounds
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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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Trimethyltin Chloride
Trimethyltin chloride is an organotin compound with the formula . It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis. Synthesis Trimethyltin chloride can be prepared by the Redistribution (chemistry), redistribution reaction of tetramethyltin with tin tetrachloride. : This is the Kocheshkov redistribution reaction. It is performed under an inert atmosphere, such as argon, typically with no solvent. A second route to involves treating the corresponding Organotin chemistry#Organotin oxides and hydroxides, hydroxide or oxide with a halogenating agent such as hydrogen chloride or thionyl chloride (): : Uses Trimethyltin chloride is used as a source of the trimethylstannyl group. For example, it is a precursor to vinyltrimethylstannane and indenyltrimethylstanane: :CH2=CHMgBr + Me3SnCl → Me3SnCH=CH2 + MgBrCl :LiC9H7 + Me3SnCl → Me3SnC9H7 + LiCl An example of an Organolithium reagent, organolithium reagent reacting with Me3SnCl to form a tin- ...
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2,2'-Bipyridine
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Double Bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were first introduced in chemical notation by Russian chemist Alexander Butlerov. Double bonds involving carbon are stronger and shorter than single bonds. The bond order is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in addition reactions of the halogens). File:Ethene structural.svg ...
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Polystannane
{{Short description, Family of inorganic polymers containing a tin-tin backbone Polystannanes are organotin compounds with the formula (R2Sn)n. These polymers have been of intermittent academic interest; they are unusual because heavy elements comprise the backbone. Structurally related but better characterized (and more useful) are the polysilanes (R2Si)n. History Oligo- or polystannanes were first described by Löwig in 1852, only 2 years after Edward Frankland's report on the isolation of the first organotin compounds. Löwig' route involved treating an Sn/K and Sn/Na alloys with iodoethane, in the presence of quartz sand which was used to control the reaction rate. Products with elemental compositions close to those of oligo(diethylstannane)s or poly(diethylstannane) were obtained. Cahours obtained similar products and attributed the formation of the so-called "stannic ethyl" to a reaction of the Wurtz type. Already in 1858, "stannic ethyl" was formulated as a polymeric c ...
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Tributyltin Hydride
Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis. Synthesis and characterization The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane: : 2 " eSi(H)Osub>n" + (Bu3Sn)2O → " eSi(OH)Osub>n" + 2 Bu3SnH The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu3Sn)2O. Its IR spectrum exhibits a strong band at 1814 cm−1 for ''ν''Sn−H. Applications It is a specialized reagent in organic synthesis. Combined with azobisisobutyronitrile (AIBN) or by irradiation with light, tributyltin hydride converts organic halides (and related groups) to the corresponding hydrocarbon. This process occurs via a radical chain mechanism involving the radical Bu3Sn•.
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