3307-88-8Relevant academic research and scientific papers
Catalytic Hydrocyanation of Activated Terminal Alkynes
Tejedor, David,Delgado-Hernández, Samuel,Colella, Lucía,García-Tellado, Fernando
supporting information, p. 15046 - 15049 (2019/11/22)
A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β-substituted acrylonitriles bearing an electron-withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle “a good nucleophile generates a strong base”, and it uses 1,4-diazabicyclo[2.2.2]octane (DABCO) as the catalyst, activated terminal alkynes as substrates and acetone cyanohydrin as the cyanide source. The acrylonitriles obtained as E,Z mixtures are straightforwardly resolved by simple flash chromatography delivering the pure isomers in preparative amounts.
Nucleophilic Addition to Oxazolium Salts: Stabilized Azomethine Ylides via 2-Substituted 4-Oxazolines
Vedejs, E.,Grissom, J.W.
, p. 1876 - 1882 (2007/10/02)
Treatment of oxazolium salts with cyanide generates 4-oxazolines 2 in situ.Ring opening to azomethine ylides 3 occurs spontaneously and 2 + 3 cycloadducts are obtained in the presence of acrylate, propiolate, or acetylenedicarboxylate dipolarophiles.In the case of acetylenic dipolarophiles, loss of HCN occurs under the reaction conditions and leads directly to pyrroles 5.The propiolate experiments are complicated by the formation of six-membered adducts 17 in some cases.This reaction pathway is explained by the addition of the acetylide anion derived from propiolate to the dipole, followed by cyclization.Sulfide nucleophiles can also be used to generate 4-oxazolines, but the yields of cycloadducts are lower.
