1,1,3,3-四(全氟己基乙基)二锡氧烷二聚体在环氧化合物开环反应中的催化作用

采用氟碳-有机溶剂两相催化体系,考察了1,1,3,3-四(全氟己基乙基)二锡氧烷二聚体(1)在环氧化合物开环反应中的催化作用.结果表明,催化剂(1)在氟碳-有机溶剂两相体系中使环氧苯乙烯和甲醇的开环反应产率高达95%,¹³CNMR谱表明,开环反应的区域选择性为100%.在氟碳-有机溶剂两相催化体系中以一锅法制备了3-苯基丙酸2-甲氧基-2-苯乙醇酯,收率高,方法简便,催化剂几乎可以定量回收循环使用.

Catalysis of 1,1,3,3-Tetrafluorohexylethyl distannoxane in the Ring-opening Reaction of Epoxides

Tetrafluorohexylethyldistannoxane compound(1) was synthesized conveniently from diphenyltin dichloride(6) by a new synthetic route, in which compound 6 reacted with R fMgI to afford Ph 2Sn(Rf)2(7) that was subjected to anhydrous hydrochloride to give (Rf)2SnCl2(8), then compound 8 was hydrolyzed with sodium hydroxide to form the fluorous tin oxide(5), the mixture(molar ratio 1:1^05) of 5 and 8 in acetone was refluxed to synthesize compound 1, the total yield was 52%. The catalysis of compound 1 was studied in the ring-opening reaction of epoxide in fluorous biphasic system. The results showed that 95% yield of the ring-opening reaction between styrene epoxide and methanol was obtained by the catalysis of compound(1) in the fluorous biphasic system. Regioselective ring-opening reaction of 100% occurred, which was confirmed by 13C NMR. 2-Methoxy-2-phenylethyl 3-phenylpropante was prepared conveniently in one pot and fluorous biphasic system at a high yield. The catalyst can be recovered qualitatively and reused without any lost almost. In summary, compound 1 was prepared in a higher yield by a new synthetic route and its catalysis was developed in the ring open reaction between epoxides and alcohol.