Efficient Activation of Acetals toward Nucleophiles by the Use of Transition Metal Salts. New Method for Cyanation of Acetals and Orthoester Derived from Aromatic and α,β-Unsaturated Carbonyl Compounds with Trimethylsilyl Cyanide under Neutral Condition
- 1 June 1989
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 18 (6) , 997-1000
- https://doi.org/10.1246/cl.1989.997
Abstract
In the presence of a catalytic amount of transition metal salts (NiCl2, CoCl2, PdCl2, etc.), trimethylsilyl cyanide smoothly reacts with acetals or orthoester derived from aromatic and α,β-unsaturated carbonyl compounds to give the corresponding α-cyano derivatives under neutral condition.Keywords
This publication has 4 references indexed in Scilit:
- Addition of trimethylsilyl cyanide to allenes with the aid of a palladium or nickel catalystTetrahedron Letters, 1986
- Cyanotrimethylsilane as a versatile reagent for introducing cyanide functionalityTetrahedron, 1983
- Regiospecificity of reactions of epoxides and oxetanes with trimethylsilyl cyanideThe Journal of Organic Chemistry, 1982
- 2-alkoxy and 2,2-dialkoxy nitriles from acetals and orthoesters — exchange of alkoxy into cyano group by means of cyanotrimethylsilaneTetrahedron Letters, 1981