86172-03-4Relevant articles and documents
CYANOTRIMETHYLSILANE AS A VERSATILE REAGENT FOR INTRODUCING CYANIDE FUNCTIONALITY
Utimoto, Kiitiro,Wakabayashi, Yukio,Horiie,Takafumi,Inoue, Masaharu,Shishiyama, Yuho,et al.
, p. 967 - 974 (2007/10/02)
Cyanotrimethylsilane adds to some α,β-unsaturated ketones in conjugate manner under the catalytic action of Lewis acids such as triethylaluminium, aluminium chloride, and SnCl2.Hydrolysis of the products gives β-cyano ketones which are identical to the hydrocyanated products of the starting enones.The title silicon reagent reacts with acetals and orthoesters under the catalytic action of SnCl2 or BF3*OEt2 affording 2-alkoxy- and 2,2-dialkoxyalkanenitriles.Application of the reaction to O-protected β-D-ribofuranoses gives selectively β-D-ribofuranosyl cyanide in excellent yield.