Collect. Czech. Chem. Commun. 1986, 51, 1094-1099

Preparation and Z-E isomerization of substituted nitrostyrenes

Ivo Bláhaa and Ladislav Lešetickýb

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Department of Organic Chemistry, Charles University, 128 40 Prague 2


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.