硒氢化钠亲核加成高收率合成对称硒醚

A convenient synthesis of symmetrical selenide with selenides sodium hydrogen via nucleophilic addition

报道了一种制备对称有机硒醚的新方法:在氮气保护下,以水做溶剂,室温下利用硼氢化钠还原硒粉得到硒氢化钠,与水溶的丙烯酸乙酯发生亲核加成反应,对于水不溶的苯乙炔或其他α,β-不饱和化合物需另加入DMF作溶剂进行反应,共合成了7个对称硒醚产物,其中6个化合物尚未见文献报道,位阻较大的甲基丙烯酸甲酯,可以得到52%的分离收率,其他产物分离收率高达82～94%。

In this paper, a new preparation method of symmetrical organoselenides was reported. In the presence of nitrogen, selenium was reduced to sodium hydrogen selenide by sodium borohydride at room temperature in water. In this solution, water soluble hydroxyethyl acrylate was added to react with sodium hydrogen selenide via nuchleophilic addition. DMF should be added to this soiution for the reactions of water insoluble phenylacetylene or other α, β-unstaturated compounds. Seven symmetrical organoselenides were afforded. Six of the products were new compounds. The products were easy to be purified by thin layer chromatograph. The product of steric hindered methyl methacrylate yielded in 52%. All the other products were obtained in yields higher of 82-94%.