Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2124-2129.DOI: 10.6023/cjoc201404048 Previous Articles     Next Articles



姚远a,b, 李伟东a, 陈建新a   

  1. a. 山西师范大学化学与材料科学学院 临汾 041004;
    b. 山西省临汾市实验中学 临汾 041000
  • 收稿日期:2014-04-25 修回日期:2014-05-21 发布日期:2014-06-16
  • 通讯作者: 陈建新
  • 基金资助:

    山西省留学回国人员基金(No. 0713)、山西省自然科学基金(No. 2012011046-9)、山西师范大学基金(No. SD2012CXSY-11)资助项目.

Synthesis of α-Siloxyamides by the Reaction of a Carbamoylsilane with Ketones

Yao Yuana,b, Li Weidonga, Chen Jianxina   

  1. a. College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004;
    b. The First Experimental Middle School of Linfen City, Linfen 041000
  • Received:2014-04-25 Revised:2014-05-21 Published:2014-06-16
  • Supported by:

    Project supported by the Foundation for Returness Overseas Scientists of Shanxi Province (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of Shanxi Normal University (No. SD2012CXSY-11).

Under using anhydrous toluene as a solvent, N,N-dimethyl carbamoyl(trimethyl)silane reacted with a series of aryl ketones or unsaturated aryl ketones at 105 ℃ to afford α-siloxyamide derivatives in good yields (60%~89%). The structures of the products were characterized by element analysis, 1H NMR, 13C NMR and IR spectra. The alkyl ketones including the alkyl-aryl ketones and alkyl-unsaturated ketones poorly reacted with N,N-dimethylcarbamoyl(trimethyl)silane. The experimental results showed that the electronic property of the substituted group on the aryl ring strongly affected the reaction. In the case of the aryl ketones with stronger donor group on the aryl ring, the longer time was needed for the reaction.

Key words: carbamoylsilane, ketones, α-siloxyamides, nucleophilic addition, synthetic methods