In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s and it was recognized in his receiving the Nobel Prize in Chemistry in 1979.
Diborane(6), generally known as diborane, is the chemical compound consisting of boron and hydrogen with the formula B2H6. It is a toxic, volatile, colorless and pyrophoric gas with a repulsively sweet odor. Synonyms include boroethane, boron hydride, and diboron hexahydride. Diborane is a key boron compound with a variety of applications. It has attracted wide attention for its electronic structure. Its derivatives are useful reagents.
An allyl group is a substituent with the structural formula H2C=CH−CH2R, where R is the rest of the molecule. It consists of a methylene bridge (−CH2−) attached to a vinyl group (−CH=CH2). The name is derived from the Latin word for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride. Allylation is any chemical reaction that adds an allyl group to a substrate.
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a reducing agent that finds application in chemistry, both in the laboratory and on an industrial scale. It has been tested as pretreatment for pulping of wood, but is too costly to be commercialized. The compound is soluble in alcohols, certain ethers, and water, although it slowly hydrolyzes.
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure C6H5CH2–. Benzyl features a benzene ring attached to a CH2 group.
Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry.
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.
In chemistry, hydroboration refers to the addition of a hydrogen-boron bond to C-C, C-N, and C-O double bonds, as well as C-C triple bonds. This chemical reaction is useful in the organic synthesis of organic compounds. The development of this technology and the underlying concepts were recognized by the Nobel Prize in Chemistry to Herbert C. Brown. He shared the Nobel prize in chemistry with Georg Wittig in 1979 for his pioneering research on organoboranes as important synthetic intermediates.
Sodium cyanoborohydride is the chemical compound with the formula NaBH3CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions.
Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH.
Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis. This colourless solid is the precursor to a range of related reagents. The compound was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes. The reagent is mainly used for the synthesis of chiral secondary alcohols.
Borane dimethylsulfide (BMS) is a complexed borane reagent that is used for hydroborations and reductions. The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. BMS is commercially available at much higher concentrations than its tetrahydrofuran counterpart and does not require sodium borohydride as a stabilizer, which could result in undesired side reactions. In contrast, borane·THF requires sodium borohydride to inhibit reduction of THF to tributyl borate. BMS is soluble in most aprotic solvents.
Cyclopentadienyliron dicarbonyl dimer is an organometallic compound with the formula [(η5-C5H5)Fe(CO)2]2, often abbreviated to Cp2Fe2(CO)4, [CpFe(CO)2]2 or even Fp2, with the colloquial name "fip dimer". It is a dark reddish-purple crystalline solid, which is readily soluble in moderately polar organic solvents such as chloroform and pyridine, but less soluble in carbon tetrachloride and carbon disulfide. Cp2Fe2(CO)4 is insoluble in but stable toward water. Cp2Fe2(CO)4 is reasonably stable to storage under air and serves as a convenient starting material for accessing other Fp (CpFe(CO)2) derivatives (described below).
Trihydridoboron, also known as borane or borine, is an unstable and highly reactive molecule with the chemical formula BH
3. The preparation of borane carbonyl, BH3(CO), played an important role in exploring the chemistry of boranes, as it indicated the likely existence of the borane molecule. However, the molecular species BH3 is a very strong Lewis acid. Consequently it is highly reactive and can only be observed directly as a continuously produced, transitory, product in a flow system or from the reaction of laser ablated atomic boron with hydrogen.
1,2-Dimethyldiborane is an organoboron compound with the formula [(CH3)BH2]2. Structurally, it is related to diborane, but with methyl groups replacing terminal hydrides on each boron. It is the dimer of methylborane, CH3BH2, the simplest alkylborane. 1,2-Dimethyldiborane can exist in a cis- and a trans arrangement. 1,2-Dimethyldiborane is an easily condensed, colorless gas that ignites spontaneously in air.
1,1-Dimethyldiborane is the organoboron compound with the formula (CH3)2B(μ-H)2BH2. A pair of related 1,2-dimethyldiboranes are also known. It is a colorless gas that ignites in air.
Pinacolborane is the borane with the formula (CH3)4C2O2BH. It features a boron hydride functional group incorporated in a five-membered C2O2B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid. It features a reactive B-H functional group.
Tetramethylethylene is a hydrocarbon with the formula Me2C=CMe2 (Me = methyl). A colorless liquid, it is the simplest tetrasubstituted alkene.
Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.
