Abstract
Abstract Olefin-palladium(II) chloride complexes reacted with n-butylamine to form Schiff’s bases. N-Ethylidene-n-butylamine was obtained by the reaction of the ethylene complex with n-butylamine, accompanied by reduction of palladium(II) to the metal. A tris(n-butylamine)palladium chloride complex was formed simultaneously by ligand substitution reaction. The yield of N-ethylidene n-butylamine was 15–19mol% (calcd on palladium) in 2.5 hr at 25°C, and decreased at temperatures higher than 60 °C with increasing reduction of palladium(II), owing to conversion of N-ethylidene-n-butylamine into either N-crotylidene-n-butylamine or a tarry polymeric substance by aldol type condensation reaction. The n-butylamine-palladium(II) chloride complex did not react with ethylene at 25°C, but reacted with ethylene at 150°C to form a large amount of tarry polymer and a small amounts of N-ethylidene-n-butylamine and N-crotylidene-n-butylamine. The propylene complex and the cyclohexene complex reacted with n-butylamine to yield both 2- and 1-N-propylidene n-butylamine, and N-cyclohexylidene-n-butylamine respectively. The yield of Schiff’s bases from olefin complex decreased in the order, ethylene>propylene>>cyclohexene.
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