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Russian Chemical Bulletin

, 60:339 | Cite as

Synthesis of isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]nitrobenzenes by nitration of the corresponding isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes

  • A. O. Finogenov
  • M. A. Epishina
  • I. V. Ovchinnikov
  • A. S. Kulikov
  • I. V. Anan’ev
  • N. N. Makhova
Full Articles

Abstract

Isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]nitro(dinitro)benzenes were synthe-sized in high yields by nitration of the corresponding 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes with a mixture of 100% nitric acid and concentrated sulfuric acid. The influence of 3- and 4-nitrofuroxanyl fragments on the regioselectivity of the nitration was revealed. The structure of 1,3-bis(4-nitrofuroxan-3-yl)-4-nitrobenzene was confirmed by X-ray diffraction analysis. 1,3- and 1,4-Bis(3-nitrofuroxan-4-yl)nitrobenzenes underwent thermal isomerization to more thermodynamically favorable 1,3- and 1,4-bis(4-nitrofuroxan-3-yl)nitrobenzenes.

Key words

isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]nitro(dinitro)benzenes nitration regioselectivity thermal isomerization X-ray diffraction analysis. 

References

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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • A. O. Finogenov
    • 1
  • M. A. Epishina
    • 1
  • I. V. Ovchinnikov
    • 1
  • A. S. Kulikov
    • 1
  • I. V. Anan’ev
    • 2
  • N. N. Makhova
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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