Reaction of Olefin-Palladium(II) Chloride Complexes with Amides

Ethylene-palladium(II) chloride complex reacts with pyrrolidone and ε-caprolactam to produce N-vinylpyrrolidone and N-vinyl-ε-caprolactam, respectively. The yield of N-vinylpyrrolidone increases with increasing reaction temperature up to 120°C and decreases above 120°C owing to conversion of N-vinylpyrrolidone to an oily polymer through thermal polymerization. By addition of quinone, the yield increases remarkably at 25°C and 90°C. Pyrrolidone - palladium(II) chloride complex, which is too stable to react with ethylene at 25°C, reacts at 120°C to give N-vinylpyrrolidone. Open chain amides such as N-ethylacetamide, acetanilide and acetamide also react with ethylene - palladium(II) chloride complex, though the corresponding N-vinylamides cannot be obtained. The reaction of a styrene - palladium(II) chloride complex with pyrrolidone was also investigated.