VINYLIC NONIONIC SUBSTITUTIONS OF ETHYL (E)-3-CHLORO-2-CYANO-3-PHENYLPROPENOATE AND (Z)-3-CHLORO-2-CYANO-3-PHENYLPROPENOATE BY ALCOHOLS

The title compounds were prepared and the stereochemistry of the nonionic vinylic substitutions by methanol, ethanol, propanol, propanol, and allylalcohol with ethyl (E)- and (Z)-3-chloro-2-cyano-3-phenylpropenoate (2E,2Z) 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 (2E and 2Z). The configuration of the reaction products were assigned from NOESY 2D NMR spectra.