The Acid-catalyzed Reaction of Isocyanide with Oxetane
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概要
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The reaction of isocyanide with oxetane in the presence of BF<SUB>3</SUB>·OEt<SUB>2</SUB> was studied; in this reaction a 1:1 cyclic adduct, 2-iminotetrahydrofuran, was formed. From 2-methyloxetane, 2-imino-5-methyltetrahydrofuran was exclusively formed. These findings suggest an S<SUB>N</SUB>2 mechanism for the cleavage of the oxetane ring. Oxetanes with electron-withdrawing substituents gave γ-alkoxybutyronitrile as the main product, along with 2-iminotetrahydrofuran. A reaction scheme involving an imidoyl cation was proposed to explain the formation of cyclic and linear products.
- 公益社団法人 日本化学会の論文
著者
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Ito Yoshihiko
Department Of Mathematics Faculty Of Education Kumamoto University
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Saegusa Takeo
Department Of Synthetic Chemistry Faculty Of Engineering Kyoto University
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Taka-ishi Naotake
Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University
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