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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1755 - 1761

DOI: https://doi.org/10.6023/cjoc201302001

Articles

Synthesis, Disproportionation and Hydrolysis Reactions of 3-Amino-4-hydroxyaminoximinofurazan

  • Zhai Lianjie ,
  • Wang Bozhou ,
  • Huo Huan ,
  • Li Hui ,
  • Li Yanan ,
  • Huang Xinping ,
  • Liu Ning ,
  • Fan Xuezhong
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  • Xi'an Modern Chemistry Research Institute, Xi'an 710065

Received date: 2013-02-01

  Revised date: 2013-04-01

  Online published: 2013-04-12

Supported by

Project supported by the National Natural Science Foundation of China (No. 21243007) and the National Defense Fundamental Scientific Research (No. B09201100051).

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Abstract

A novel energetic intermediate 3-amino-4-hydroxyaminoximinofurazan (DOAF) was synthesized from 3-amino-4-amidoximinofurazan (DAOF) via diazotisation and oximation reactions with a total yield of 61.8%, and its structure was characterized by NMR, IR, MS and elemental analysis. The main factors for the oximation reaction were thoroughly studied, and the optimum reaction conditions were found to be as follows: the materials ratio n(ACOF):n(NH2OH·HCl):n(CH3ONa) was 1:2:3, reaction temperature 30℃, and reaction time 2 h with a yield of 86.5%. It was found that 3-amino-4-hydroxyaminoximinofurazan (DOAF) was disproportionated to obtain two compounds under alkaline condition, which were identified as 3-amino-4-nitrosoximinofurazan potassium salt and DAOF. Moreover, DOAF was hydrolyzed to give a new product in acidic aqueous solution, which was identified as 3-amino-4-(N-hydroxyamido)furazan. The single crystal of K(DNOF)·H2O was obtained and its crystal belong to monoclinic system, space group is P2(1)/c, cell parameters are a=0.7639(19) nm, b=0.7034(17) nm, c=1.436(4) nm, α=90°, β=101.025(3)°, γ=90°, V=0.7573(3) nm3, Z=4, Dc=1.870 g·cm-3, μ=0.695 mm-1, F(000)=432, R1=0.0349 and wR2=0.1027.

Key words： 3-amino-4-hydroxyaminoximinofurazan; energetic intermediate; synthesis; disproportionation; hydrolysis; crystal structure

Cite this article

Zhai Lianjie , Wang Bozhou , Huo Huan , Li Hui , Li Yanan , Huang Xinping , Liu Ning , Fan Xuezhong . Synthesis, Disproportionation and Hydrolysis Reactions of 3-Amino-4-hydroxyaminoximinofurazan[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1755 -1761 . DOI: 10.6023/cjoc201302001

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