106836-06-0Relevant academic research and scientific papers
Regiospecific Ring Opening of Epoxides with Cyanotrimethylsilane on Solid Bases: Reaction Features, and Role of Metal Cations of Solid Bases
Sugita, Keisuke,Ohta, Akihisa,Onaka, Makoto,Izumi, Yusuke
, p. 1792 - 1799 (2007/10/02)
A new attempt of utilizing solid acids and bases for ring opening of epoxides with Me3SiCN was investigated.Solid strong bases such as calcium oxide and magnesium oxide catalyzed the regio- and chemoselective ring opening of epoxides with Me3SiCN much more effectively than homogeneous catalysts.On CaO and MgO, the reactions of unsymmetrical epoxides with Me3SiCN 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 Me3SiCN, and simultaneously calcium ions promoted the ring opening of epoxyalkanol as Lewis acid sites.
Reaction of Cyanotrimethylsilane with Oxiranes. Effect of Catalysts or Mediators on Regioselectivity and Ambident Character
Imi, Katsuharu,Yanagihara, Naoto,Utimoto, Kiitiro
, p. 1013 - 1016 (2007/10/02)
Reaction of cyanotrimethylsilane with oxiranes under the catalytic action of Lewis acids Pd(CN)2, SnCl2, or Me3Ga affords 2-trimethylsiloxy isocyanides by regio- and stereoselective attack of isocyanide on the more substituted carbon.The reaction mediated by aluminium alkoxides gives predominantly 3-trimethylsiloxy nitriles by the selective attack of cyanide on the less substituted carbon.
