Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (03): 409-413. Previous Articles     Next Articles

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  1. (a北京理工大学化工与环境学院 北京 100081)
    (b西安近代化学研究所 西安 710061)
  • 收稿日期:2009-07-13 修回日期:2009-09-14 发布日期:2010-03-28
  • 通讯作者: 孟子晖

Reaction Mechanism for the Formation of 1,3-Ditertiobutyl-5,5-

Li Qingxiaa,Wang Penga,Meng Wenjuna,Meng Zihui*,a,Lou Zhonglianga
Song Hongyana,Qin Guangmingb,Ge Zhongxueb,Wang Bozhoub

  1. (a School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081)
    (b Xi'an Morden Chemistry Research Insitute, Xi'an 710061)
  • Received:2009-07-13 Revised:2009-09-14 Published:2010-03-28

The key precursor of the energetic plasticizer 1,3,5,5-tetranitrohexahydropyrimidine is 1,3-diter- tiobutyl-5,5-dinitrohexahydropyrimidine, which was synthesized from 2,2-dinitropropane-1,3-diol, formaldehyde and tert-butylamine via Mannich reaction. A stable intermediate N-benzyl-2,2-dinitroethylamine was obtained, and isotope tracing experiment was employed to elucidate the reaction process, and finally a synthetic mechanism for 1,3-ditertiobutyl-5,5-dinitrohexahydropyrimidine was proposed.

Key words: 2,2-dinitropropane-1,3-diol, 1,3-ditertiobutyl-5,5-dinitrohexahydropyrimidine, Mannich reaction, synthetic mechanism