Vinylic Nonionic Substitutions of Ethyl (E)- and (Z)-3-Chloro-2-cyano-3-phenylpropenoate by Alcohols

Abstract

The title compounds were prepared and the stereochemistry of the nonionic vinylic substitutions by methanol, ethanol, propanol, 2-propanol, and allylalcohol with ethyl (E)- and (Z)-3-chloro-2-cyano-3-phenylpropenoate (2 E,2 Z) in the presence of potassium carbonate, triethylamine and N-methyl-2-pyrrolidone were studied. The reactions with the alcohols gave ethyl (E)-3-alkoxy-2-cyano-3-phe- nylpropenoate, independent of the configuration of the starting chloropropenoate (2 E and 2 Z). The configuration of the reaction products were assigned from NOESY 2D NMR spectra.