Selectivity of Reactions of Methylhydrazones with Butadiene in the Presence of Palladium and Nickel Complexes.

Abstract

Reactions of aldehyde and ketone methylhydrazones with butadiene in the presence of palladium complexes have been shown to yield N-octadienylated methylhydrazones. In contrast, in the presence of nickel complexes, a mixture of two isomeric azo-derivatives are formed from two moles of butadiene and one mole of methylhydrazone. The selectivity of these reactions is discussed in terms of the reactivity of the bis-π-allylmetal intermediates.