18151-32-1Relevant articles and documents
β-Cyanoethyl anion: Lusus naturae
Merrill, Grant N.,Dahlke, Gregg D.,Kass, Steven R.
, p. 4462 - 4468 (1996)
A stable El(cb) intermediate, β-cyanoethyl anion (1β), has been synthesized in the gas phase at room temperature under thermal conditions via the fluoride-induced desilylation of 3-(trimethylsilyl)propionitrile. The reactivity and thermodynamic properties of this ion are reported. The cyano group is found to lower the proton affinity of 1β by 29 ± 6 kcal/mol, which represents a particularly large substituent effect. High-level ab initio and density functional calculations have been carried out on 1β and several related species. The computational results are compared to each other, and their accuracy is evaluated.
Cobalt Carbonyl Catalyzed Hydrosilylation of Nitriles: A New Preparation of N,N-Disilylamines
Murai, Toshiaki,Sakane, Takehiko,Kato, Shinzi
, p. 449 - 453 (2007/10/02)
Cobalt carbonyl catalyzed hydrosilylation of a wide variety of nitriles with HSiMe3 has been examined.The reaction generally proceeded at 60 deg C to give N,N-disilylamines in good yields.Electron-donating groups on aromatic nitriles facilitated the react
β-Silylcarbonyl Compounds as Masked Enones
Fleming, Ian,Goldhill, Jon
, p. 1493 - 1498 (2007/10/02)
β-Trimethylsilylketones and lactones can be brominated (3)->(4) and desilylbrominated (4)->(5) specifically to place a double bond between the carbonyl group and the β-carbon atom to which the silicon had originally been bound.The silyl group therefore is a base- and acid stable group masking the α,β-unsaturation of enones.Several α-methylene-ketones and -lactones have been prepared in this way.With ketones, the bromination step seems always to introduce bromine mainly or exclusively at the α-position on that side of the ketone on which the β-silyl group is placed, regardless of whether it is more or the less substituted α-position.
