Preparation and Z-E isomerization of substituted nitrostyrenes

Abstract

This study concerns the synthesis of β-sustituted β-nitrostyrenes by two procedures: addition of nitryl halogenides to double bonds, connected with the elimination of hydrogen halide, and condensation of aldehydes with substituted nitromethanes, and it compares the utilizability of the two procedures. Two of the substances prepared, methyl (Z)-nitro-3-phenylpropenoate and (Z)-4-phenyl-β-nitro-β-buten-2-one, were submitted to Z-E isomerization at various temperatures, and thermodynamic isomerization parameters were estimated from the dependence of the equilibrium constants on temperature.