Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (04): 741-745. Previous Articles     Next Articles

Reports

二茂铁四唑和二茂铁甲醛缩3-取代丙二醇衍生物的合成

张慧卿a,b,周智明*,a,方敏a   

  1. (a北京理工大学化工与环境学院 北京 100081)
    (b北京化工大学理学院 北京 100029)
  • 收稿日期:2006-12-25 修回日期:2007-11-07 发布日期:2008-04-17
  • 通讯作者: 周智明

Synthesis of Novel Ferrocenyl Tetrazole and 3-Substituted Acetal Derivatives

ZHANG Hui-Qinga,b,ZHOU Zhi-Ming*,a,FANG Mina   

  1. (a School of Chemical Engineering and the Environment, Beijing Institute of Techology, Beijing 100081)
    (b School of Science, Beijing University of Chemical Technology, Beijing 100029)
  • Received:2006-12-25 Revised:2007-11-07 Published:2008-04-17
  • Contact: ZHOU Zhi-Ming

Condensation of the prepared formyl ferrocene 6 with hydroxylammonium chloride gave ferrocenyl oxime 7, which was dehydrated to produce ferrocenyl nitrile 8. This nitrile was converted to new ferrocenyl tetrazol (9) using (n-C4H9)3SnCl and NaN3. In the presence of toluene-4-sulfonic acid (PTSA) the reaction between formyl ferrocene 6 and trimethyl orthoformate gave dimethyl acetal 10. Transacetalization of acetal 10 with (R)-(-)-3-chloro-1,2-propanediol furnished new ferrocenyl acetal 12, which was converted to ferrocenyl acetal 13 by a reaction with NaN3. The new ferrocenyl acetal 15 was obtained by a reaction of acetal 10 with (R)-(-)-1-methoxy-2,3-propanediol (14), which was obtained by a reaction of (R)-(-)-3- chloro-1,2-propanediol with CH3OH in the presence of NaOH. All of these new compounds were characterized by MS, 1H NMR and IR spectra.

Key words: tetrazole, ferrocene, acetal, synthesis