104919-31-5Relevant articles and documents
trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines
Meyer, Maximilian,Peri?, Milica,Sch?mberg, Fritz,Vilotijevi?, Ivan
supporting information, (2021/10/04)
trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.
Phosphine-catalyzed reaction of cyanohydrins with activated alkynes
Siby, Acetou,Loreau, Olivier,Taran, Frederic
experimental part, p. 2365 - 2370 (2010/02/28)
A new method for preparing α-cyanoacrylates and α-cyanoenones is described. The procedure uses a phosphine-catalyzed α-C addition of cyanide ion, generated in situ from cyanohydrins, to activated alkynes. An unexpected tandem reaction producing benzyliden
ISOXAZOLINE OXIDATION. AN EFFICIENT METHOD FOR THE PREPARATION OF α,β-UNSATURATED CARBONYL COMPOUNDS
Padwa, Albert,Kline, Donald N.,Perumattam, John
, p. 913 - 916 (2007/10/02)
MCPBA peracid oxidation of Δ4-isoxazolines derived from the dipolar cycloaddition reaction of nitrones with acetylenes or allenes produces α,β-unsaturated ketones in excellent yield.