高等学校化学学报

高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (9): 1662.

• 研究论文 • 上一篇    下一篇

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

向建南1, 尹霞1, 陈超越1, 樊红莉1, 何纯连2   

  1. 1. 湖南大学化学化工学院, 长沙410082;
    2. 湖南师范大学医学院, 长沙410006
  • 收稿日期:2002-07-10 出版日期:2004-09-24 发布日期:2004-09-24
  • 基金资助:

    湖南省自然科学基金(批准号:02JJY4009和03JJY3016);湖南大学博士人才基金(批准号:531103011056)资助

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

XIANG Jian-Nan1, YIN Xia1, CHEN Chao-Yue1, FAN Hong-Li1, HE Chun-Lian2   

  1. 1. College of Chemistry & Chemical Engineering, Hunan University, Changsha 410082, China;
    2. College of Medicine, Hunan Normal University, Changsha 410006, China
  • Received:2002-07-10 Online:2004-09-24 Published:2004-09-24

PDF (PC)

被引次数

13

摘要： 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.

关键词: 1, 1, 3, 3-四(全氟己基乙基)二锡氧烷二聚体, 环氧化合物, 开环, 区域选择性, 氟碳两相体系

Abstract: 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.

Key words: 1,1,3,3-Tetrafluorohexylethyldistannoxane, Epoxide, Ring open reaction, Regioselectivity, Fluorous bipasic system

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