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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.
Methylcyclopentane is an organic compound with the chemical formula CH 3 C 5 H 9.It is a colourless, flammable liquid with a faint odor. It is a component of the naphthene fraction of petroleum usually obtained as a mixture with cyclohexane.
Many alternative routes are available for producing alcohols, including the hydroboration–oxidation reaction, the oxymercuration–reduction reaction, the Mukaiyama hydration, the reduction of ketones and aldehydes and as a biological method fermentation.
Hydroboration of trisubstituted alkenes places boron on the less substituted carbon. [7] Hydroboration of 1,2-disubstituted alkenes, such as a cis or trans olefin, produces generally a mixture of the two organoboranes of comparable amounts, even if the steric properties of the substituents are very different. For such 1,2-disubstituted olefins ...
Cyclopentene was first prepared by Carl Gärtner in 1893 from iodocyclopentane with potassium hydroxide.He named it pentamethenylene (German: Pentamethenylen). [3] ...
Hydroboration occurs stereospecifically syn — on the same alkene face. The transition state for this concerted reaction can be visualized as a square with the corners occupied by carbon, carbon, hydrogen and boron, maximizing overlap between the olefin p-orbitals and the empty boron orbital.
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Wilkinson's catalyst also catalyzes many other hydrofunctionalization reactions including hydroacylation, hydroboration, and hydrosilylation of alkenes. [14] Hydroborations have been studied with catecholborane and pinacolborane. [15] It is also active for the hydrosilylation of alkenes. [16]