Chem. J. Chinese Universities ›› 2004, Vol. 25 ›› Issue (9): 1662.

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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

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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