Chem. J. Chinese Universities ›› 1990, Vol. 11 ›› Issue (12): 1367.

• Articles • Previous Articles     Next Articles

A New Route for the Synthesis of Ferrocenyl a-Diketones

Shi Shu-jian, An Rong, Yuan Han-cheng   

  1. Deportment of Applied Chemistry, Beijing Institute of Chemical Technology, Beijing, 100029
  • Received:1990-03-09 Online:1990-12-24 Published:1990-12-24

Abstract: Anew route for the synthesis of ferrocenyl a-diketones has been developed. The method consists of reacting formylferrocene with propanedithiol-1, 3 to form ferrocenyl dithiane, which is lithiated with BuLi to yield lithiodithiane of ferrocene, and this intermediate is then treated with esters. The addition products of ferrocenyl dithiane are finally hydrolyzed in the presence of HgCl2-CdCO3 to give the subject prodcuts. All the synthesized ferrocenyl dithiane and a-diketoncs, except Ia and Ic, are new compounds with their structures comfirmed by elemental analysis, 1R and 1H NMR. The yields of the synthesis are moderately good. Only in two cases the yields are low, the reasons for which are proposed. It is also distinct from that reported in the previous literatures in two respects : there is no 2 : 1 addition product formed in the synthesis, and all the ferrocenyl acyl dithiancs arc very easily hydrolysable with HgCl2-CdCO3. These unexpected results are tentatively explained. Abrief discussion for the IR and 1H NMRof the products is given.

Key words: Ferrocene, Dithiane, a-Diketone

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