Reaction of Olefin-Palladium(II) Chloride Complexes with <I>n</I>-Butylamine

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概要

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• Olefin-palladium(II) chloride complexes reacted with <I>n</I>-butylamine to form Schiff's bases. <I>N</I>-Ethylidene-<I>n</I>-butylamine was obtained by the reaction of the ethylene complex with <I>n</I>-butylamine, accompanied by reduction of palladium(II) to the metal. A tris(<I>n</I>-butylamine)palladium chloride complex was formed simultaneously by ligand substitution reaction. The yield of <I>N</I>-ethylidene <I>n</I>-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 <I>N</I>-ethylidene-<I>n</I>-butylamine into either <I>N</I>-crotylidene-<I>n</I>-butylamine or a tarry polymeric substance by aldol type condensation reaction. The <I>n</I>-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 <I>N</I>-ethylidene-<I>n</I>-butylamine and <I>N</I>-crotylidene-<I>n</I>-butylamine. The propylene complex and the cyclohexene complex reacted with <I>n</I>-butylamine to yield both 2- and 1-<I>N</I>-propylidene <I>n</I>-butylamine, and <I>N</I>-cyclohexylidene-<I>n</I>-butylamine respectively. The yield of Schiff's bases from olefin complex decreased in the order, ethylene>propylene>>cyclohexene.

• 公益社団法人 日本化学会の論文

著者

• Sawai Hiroaki

  Department Of Applied Chemistry Faculty Of Engineering Gunma University

• Hirai Hidefumi

  Department Of Industrial Chemistry Faculty Of Engineering Science University Of Tokyo

• Makishima Shoji

  Department of Industrial Chemistry, Faculty of Engineering, The University of Tokyo

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