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KMID : 1059519870310010025
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Journal of the Korean Chemical Society
1987 Volume.31 No. 1 p.25 ~ p.30
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Solvation in Mixed Solvents (Part Ⅴ) : Solvolysis of tert-Butyl Halides and 1-Adamantyl Tosylate in Methanol-Acetone Mixtures
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Lee Ik-Choon
Lah Sang-Moo
Kong Byung-Hoo
Lee Bon-Su
Sohn Se-Chul
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Abstract
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Solvolysis of tert-butyl halides and 1-adamantyl tosylate in methanol-acetone mixtures and solvolysis of tert-butyl bromide in methanol-chloroform mixtures have been studied. Solvent ionizing power of methanol-acetone mixtures were calculated by the Grunwald-Winstein equation and discussed the Y value variation caused by substrate changes. Y values based on 1-adamantyl tosylate is superion to others since it varies in wide range for methanol-acetone mixtures. It was found that the order of electrophilic assistance to leaving group is OTs > Cl > Br > I.
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