14631-45-9Relevant academic research and scientific papers
2-ALKOXY AND 2,2-DIALKOXY NITRILES FROM ACETALS AND ORTHOESTERS --- EXCHANGE OF ALKOXY INTO CYANO GROUP BY MEANS OF CYANOTRIMETHYLSILANE
Utimoto, Kiitiro,Wakabayashi, Yukio,Shishiyama, Yuho,Inoue, Masaharu,Nozaki, Hitosi
, p. 4279 - 4280 (1981)
Title transformation is accomplished by the catalytic action of SnCl2 or BF3*OEt2.Lithio derivative of 2,2-dimethoxyacetonitrile is used as synthetic equivalent of methyl lithioformate.
TRIMETHYLSILYL CYANIDE PROMOTED CYANATION OF TERTIARY ALKYL CHLORIDES AND OTHER SN1 ACTIVE COMPOUNDS
Reetz, Manfred T.,Chatziiosifidis, Ioannis,Kuenzer, Hermann,Mueller-Starke, Hans
, p. 961 - 966 (2007/10/02)
Tertiary chlorides are readily cyanated in a one-pot procedure using trimethylsilyl cyanide in the presence of SnCl4.The mechanism of this novel and synthetically useful reaction involves initial isonitrile formation followed by rearrangement to the tertiary nitrile.Other SN1 active compounds also undergo smooth cyanation.
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.
