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Crown ether adducts of light alkali metal triphenylsilyls: synthesis, structure and hydrosilylation catalysis
Valeri Leich1, Kevin Lamberts, Thomas P Spaniol
1Institute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany. jun.okuda@ac.rwth-aachen.de.
Abstract:
Alkali metal triphenylsilyls [Li(12-crown-4)SiPh3]·(thf)0.5 (2), [Na(15-crown-5)SiPh3]·(thf)0.5 (3) and [K(18-crown-6)SiPh3(thf)] (4) were synthesized using 1,1,1-trimethyl-2,2,2-triphenyldisilane (Ph3SiSiMe3) and isolated in high yields. Solid state structures were determined by single crystal X-ray diffraction. These alkali metal silyls catalyzed the regioselective hydrosilylation of 1,1-diphenylethylene to give the anti-Markovnikov product. The presence of crown ethers enhanced the reactivity of the metal silyls in hydrosilylation catalysis.
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02:36Crown Ethers
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Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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