Collect. Czech. Chem. Commun. 1987, 52, 1280-1284

Addition of esters of chloroacetic acids to 1,3-butadiene catalysed by copper complexes

Zdeněk Vít and Milan Hájek

Institute of Chemical Process Fundamentals, Czechoslovak Academy of Sciences, 165 02 Prague 6-Suchdol


The addition of alkyl trichloro- and dichloroacetates to 1,3-butadiene catalysed by copper complexes has been studied. The reactivity of the chloroacetates increased with increasing number of chlorine atoms in their molecule and with decreasing number of the carbon atoms of the alkyl of their ester group. The addition of trichloroacetates gave the products (1 : 1 adducts) in around 80 percent yields while the less reactive dichloroacetates afforded the adducts in 35% yields. The 1 : 1 adducts were the products of both 1,4- and 1,2-addition, the relative proportion of which depended especially on the type of the ligand of copper complexes.