Regiospecific Ring Opening of Epoxides with Cyanotrimethylsilane on Solid Bases: Reaction Features, and Role of Metal Cations of Solid Bases.
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概要
- 論文の詳細を見る
A new attempt of utilizing solid acids and bases for ring opening of epoxides with Me<SUB>3</SUB>SiCN was investigated. Solid strong bases such as calcium oxide and magnesium oxide catalyzed the regio- and chemoselective ring opening of epoxides with Me<SUB>3</SUB>SiCN much more effectively than homogeneous catalysts. On CaO and MgO, the reactions of unsymmetrical epoxides with Me<SUB>3</SUB>SiCN afforded 3-trimethylsiloxyalkanenitriles in high yields through regio- and stereoselective attack of cyanide ion on the less substituted epoxycarbon. Additionally, on CaO, 2,3-epoxy-1-alkanol derivatives were selectively converted to the corresponding C-3 opened products by the attack of cyanide ion. In these cases no isocyanides were formed. It was suggested that CaO acted as a bifunctional catalyst; the lattice oxide anions of CaO activated Me<SUB>3</SUB>SiCN, and simultaneously calcium ions promoted the ring opening of epoxyalkanol as Lewis acid sites.
- 公益社団法人 日本化学会の論文
著者
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Izumi Yusuke
Department of Cardiology Ogakii Municipal Hospital
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ONAKA Makoto
Department of Applied Chemistry, Faculty of Engineering, Nagoya University
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Ohta Akihisa
Department of Synthetic Chemistry, School of Engineering, Nagoya University
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Sugita Keisuke
Department of Synthetic Chemistry, School of Engineering, Nagoya University
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Izumi Yusuke
Department of Synthetic Chemistry, School of Engineering, Nagoya University
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