水溶媒中での3-クロルメチル-3-ヒドロキシメチルオキセタンおよびペンタエリトリットジクロルヒドリンと水酸化ナトリウ厶の反応に関する研究

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Reactions between sodium hydroxide and 3-chloromethyl-3-hydroxymethyloxetane (I) or pentaerythritol dichlorohydrin (II) in water have been studied to clarify the following:1. The amount of solvent water markedly affects the mode of reactions of (I). When the reaction was conducted in a large volume of water, the main product was2, 6-dioxaspiro[3, 3]heptane. Such ring closure reaction was overcome by intermolecular reacthions when the solvent volume was reduced. 2. 3-Methyleneoxetane, 3, 3-bishydroxymethyloxetane, and 2, 6, 8-trioxaspiro[3, 5]nonane were identified as by-products. A dimeric product was also isolated as an intermolecularly reacted product and its chemical structure has been proposed.3. The reaction velocity of pentaerythritol dichlorohydrin to form 3-chloromethyl-3-hydroxymethyloxetane is approximately 50 fold that for the formation of 2, 6-dioxaspiro[3, 3]heptane.4. Using water as a reaction medium, 2, 6-dioxaspiro[3, 3]heptane, was obtained in 50-60% yield.
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