The effect of macrocyclic polyethers on the alkylation of sodium 2-naphtholate.
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概要
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The alkylation of sodium 2-naphtholate, in the presence of benzo-18-crown-6 or 4,7,13,16,21,24-hexaoxabicyclo[8.8.8]hexacosane is found to give high ratios of <I>O</I>/<I>O</I>+<I>C</I> alkylation when conducted in THF, in benzene, and in water. The striking increase in the product ratio is attributed to a specific complexation of the macrocyclic polyethers, which facilitate the dissociation of the ion-pair aggregate of the sodio-derivative which exists in benzene or THF. The polyethers may act as phase-transfer catalysts when the reaction is run in water. In support of this conclusion, the reaction in DMF or acetonitrile, in which the dissociation of sodium 2-naphtholate takes place, fails to show any effect of the macrocyclic polyethers on the product ratio.
- 公益社団法人 日本化学会の論文
著者
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Akabori Sadatoshi
Department Of Chemistry Faculty Of Science Toho University
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Akabori Sadatoshi
Department of Chemistry, Faculty of Science, T\={o}ho University
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Tuji Hiroyuki
Department of Chemistry, Faculty of Science, T\={o}ho University
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