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Russian Chemical Bulletin

, Volume 57, Issue 3, pp 638–643 | Cite as

Synthesis, structure, and properties of N-(nitramino)phthalimide

  • M. S. Klenov
  • A. M. Churakov
  • O. V. Anikin
  • Yu. A. Strelenko
  • I. V. Fedyanin
  • K. A. Lyssenko
  • V. A. Tartakovsky
Full Articles

Abstract

N-(Nitramino)phthalimide R2N-NHNO2 (R2NH is phthalimide) was synthesized by nitration of N-aminophthalimide with nitronium tetrafluoroborate. The structure of this compound was established by X-ray diffraction and confirmed by 1H, 13C, and 14N NMR spectroscopy. The methylation of this compound with diazomethane affords a mixture of N-methyl (R2N-NMeNO2) and O-methyl (R2N-N=N(O)OMe) isomers. The latter compound contains the previously unknown high-nitrogen-oxygen fragment. The thermal decomposition of N-(nitramino)phthalimide in vacuo at 80–100 °C gives 2H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride) as the major product.

Key words

primary nitramines nitrohydrazines diazomethane nitronium tetrafluoroborate nitration thermolysis X-ray diffraction study NMR 

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References

  1. 1.
    F. R. Benson, The High Nitrogen Compounds, Wiley, New York, 1984, 679 pp.Google Scholar
  2. 2.
    A. V. Kalinin, E. T. Apasov, S. L. Ioffe, V. A. Tartakovsky, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1108 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 988 (Engl.Transl.)].Google Scholar
  3. 3.
    R. N. Haszeldine, A. E. Tipping, J. Chem. Soc. C, 1966, 1236.Google Scholar
  4. 4.
    M. G. Barlow, K. W. Cheung, J. Fluor. Chem., 1977, 10, 191.CrossRefGoogle Scholar
  5. 5.
    W. O. Wootton, J. Chem. Soc., 1907, 91, 1890.Google Scholar
  6. 6.
    A. R. Katritzky, J. Lewis, S. Q. Abbas Rizvi, G. Roch, Anales de Quimica, 1974, 70, 994.Google Scholar
  7. 7.
    S. L. Ioffe, L. M. Makarenkova, A. L. Blyumenfel’d, I. A. Maslina, V. A. Tartakovsky, Izv. Akad. Nauk SSSR, Ser. Khim., 1976, 2326 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1976, 25, 1976 (Engl.Transl.)].Google Scholar
  8. 8.
    D. F. Reit in The Chemistry of the Nitro and Nitroso Groups, Ed. H. Feuer, Wiley, New York, 1969.Google Scholar
  9. 9.
    J. Bergman, T. Brimert, Tetrahedron, 1999, 55, 5581.CrossRefGoogle Scholar
  10. 10.
    A. H. Lamberton, H. M. Yusuf, J. Chem. Soc. C, 1969, 397.Google Scholar
  11. 11.
    F. I. Dubovitskii, B. L. Korsunskii, Usp. Khim., 1981, 50, 1828 [Russ. Chem. Rev., 1981, 50 (Engl.Transl.)].Google Scholar
  12. 12.
    Yu. Shu, B. L. Korsunskii, G. M. Nazin, Usp. Khim., 2004, 73, 320 [Russ. Chem. Rev., 2004, 73 (Engl.Transl.)].Google Scholar
  13. 13.
    R. S. Stepanov, A. M. Astakhov, Yu. V. Kekin, L. A. Kruglyakova, Zh. Org. Khim., 1997, 33, 1632 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].Google Scholar
  14. 14.
    D. W. Jones, J. Chem. Soc., Perkin Trans. I, 1976, 115.Google Scholar
  15. 15.
    D. Ben-Ishai, E. Katchalski, J. Am. Chem. Soc., 1952, 74, 3688.CrossRefGoogle Scholar
  16. 16.
    M. Gütschow, J. Org. Chem., 1999, 64, 5109.CrossRefGoogle Scholar
  17. 17.
    D. W. Ball, J. Mol. Struct.: THEOCHEM, 2006, 773, 1.CrossRefGoogle Scholar
  18. 18.
    J. H. Loehlin, Acta Crystallogr., Sect. C, 1985, 41, 210.CrossRefGoogle Scholar
  19. 19.
    C. S. Choi, E. Prince, Acta Crystallogr., Sect. B, 1972, 28, 2857.CrossRefGoogle Scholar
  20. 20.
    Y. Kohno, K. Maekawa, T. Tsuchioka, T. Hashizume, A. Imamura, Chem. Phys. Lett., 1993, 214, 603.CrossRefGoogle Scholar
  21. 21.
    H. D. K. Drew, H. H. Hatt, J. Chem. Soc., 1937, 16.Google Scholar
  22. 22.
    F. Arndt, in Organic Syntheses, coll. vol. 2, New York, Wiley, 1946, p. 165.Google Scholar
  23. 23.
    A. A. Granovsky, PC GAMESS version 7.1, http://classic.chem.msu.su/gran/gamess/index.html.

Copyright information

© Springer Science+Business Media, Inc.  2008

Authors and Affiliations

  • M. S. Klenov
    • 1
  • A. M. Churakov
    • 1
  • O. V. Anikin
    • 1
  • Yu. A. Strelenko
    • 1
  • I. V. Fedyanin
    • 2
  • K. A. Lyssenko
    • 2
  • V. A. Tartakovsky
    • 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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