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Kinetic and NMR spe...
Kinetic and NMR spectroscopic studies of chiral mixed sodium/lithium amides used for the deprotonation of cyclohexene oxide.
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- Sott, Richard, 1974 (författare)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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- Granander, Johan, 1975 (författare)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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Williamson, Carl (författare)
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- Hilmersson, Göran, 1966 (författare)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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(creator_code:org_t)
- Wiley, 2005
- 2005
- Engelska.
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Ingår i: Chemistry (Weinheim an der Bergstrasse, Germany). - : Wiley. - 0947-6539. ; 11:16, s. 4785-92
- Relaterad länk:
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https://gup.ub.gu.se...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- The mixed-metal complex formed from n-butylsodium, n-butyllithium, and a chiral amino ether has been studied by NMR spectroscopy. Three different mixed-metal amides were used as chiral bases for the deprotonation of cyclohexene oxide. The selectivity and initial rate of reaction were compared for sodium-amido ethers, lithium-amido ethers, and mixtures of sodium and lithiumamido ethers in diethyl ether and tetrahydrofuran, respectively. The mixed sodium/lithium amides are more reactive than the single sodium and lithium amides, whereas the stereoselectivities are higher when lithium amides are used. The alkali-metal/gamma-amido ethers exhibit both higher initial reaction rates and stereoselectivities than their beta-amido ether analogues. NMR spectroscopic studies of mixtures of n-butylsodium (nBuNa), n-butyllithium (nBuLi), and the gamma-amino ethers in diethyl ether show the exclusive formation of dimeric mixed-metal amides. In diethyl ether, the lithium atom of the mixed-metal amide is internally coordinated and the sodium atom is exposed to solvent; however, in tetrahydrofuran, both metals are internally coordinated.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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