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[[alternative]]The reaction of the B-nitrostyrene and Grignard reagents

By [[author]]林育玫, Yu Mei [[author]]Lin, 林育玫 and Yu Mei Lin


[[abstract]]β-nitrostyrene 及其相關雜環化合物可和格里納試劑於低溫下反應生 成1,4-加成體,若將此1,4-加成體加入冰浴的稀鹽酸水溶液中則產生 nitroalkanes。倘加入冰浴濃硫酸水溶液則生成carboxyic acids。但如 果使用冰浴濃鹵酸水溶液則可產生hydroximoylhalides。Hyroximoyl halides可轉變成nitrile oxides,與不飽和之烯類化合物進行1,4-加成反 應在合成上應用廣泛。 Reactions of β-nitrostyrene and Grignard Reagents gave 1,4-adducts(nitronates) at -20 ℃.Futher manipulation of the nitronate were demostrated as follows:(1) treatment of the nitronates with 0 ℃ 5% HCl(aq) generated nitroalkanes. (2) tretment of the nitronates with 0 ℃ 85% H2SO4(aq)generated caboxylic acids. (3) tretment of the nitronates with 0℃ conc. HX(aq) generated hydroximoyl halides. Hydroximoyl halides could convert to nitrile oxide in the presence of base such as triethyl amine, followed by 1,3-dipolar cycloaddition with alkenes or alkynes to give 2-isoxazolines or isoxazoles. Reactions of β-nitrostyrene and Grignard Reagents gave

Topics: B-硝基化合物, 格里納試劑, nitroalkane, B-nitroalkene, hydroximoyl halide, 1,3-dipolar, [[classification]]39
Year: 2010
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