Chemistry of Palladium Complexes

Abstract

The vinylation of acetic acid by higher olefins has been studied. Using the hexenes as model compounds, the struc tures of the products have been elucidated both for the vinylation products and for the higher boiling materials pro duced under certain conditions. The effect of several reac tion parameters on the course of the reaction has been studied. Both the ratio of vinylation products to higher boiling products and the distribution of isomers within the vinyl esters depend on the relative amount of acetate ion present. High levels of specific vinyl esters could be pro duced by the correct choice of olefin and reaction parame ters. With α-olefins, primary esters could be produced with greater than 75% specificity. As an alternate for the cur rently accepted vinylation mechanism, a new reaction pathway is proposed.Cince the first report of synthesizing vinyl acetate from ethylene (37), ^ a number of other reports on this reaction ( Reaction 1 ) have appeared (4,