7515-17-5Relevant articles and documents
Oxidation of aromatic compounds: XI. Oxidation of methyl 3-(4-methoxyphenyl)propynoate in the system CF3COOH-CH 2Cl2-PbO2
Vasilyev,Fundamenskii,Savchenkov,Rudenko
, p. 860 - 862 (2003)
Oxidation of methyl 3-(4-methoxyphenyl)propynoate in the system CF 3COOH-CH2Cl2-PbO2 at 0-2°C within 2 h affords in a preparative yield of 55% a product of oxidative dimerization, dimethyl 2,3-bis(4-methoxyphenylcarbonyl)but-2-ene-1,4- dicarboxylate (II) whose double bond is in E-configuration according to X-ray diffraction data.
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.
Organocatalytic trans Phosphinoboration of Internal Alkynes
Fritzemeier, Russell G.,Nekvinda, Jan,Rosenblum, Carol Ann,Santos, Webster L.,Slebodnick, Carla,Vogels, Christopher M.,Westcott, Stephen A.
supporting information, p. 14358 - 14362 (2020/07/04)
We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.