Russian Journal of Organic Chemistry

, Volume 40, Issue 8, pp 1140–1145 | Cite as

Reaction of Endic Anhydride with Hydrazines and Acylhydrazines

  • O. V. Krishchik
  • I. N. Tarabara
  • A. O. Kas'yan
  • S. V. Shishkina
  • O. V. Shishkin
  • A. K. Isaev
  • L.I. Kas'yan
Article

Abstract

Reaction products of bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboxylic (endic) acid with hydrazines and acylhydrazines were prepared. The features distinguishing of these reactions from those with amines were revealed. The compounds obtained were characterized by 1H, 13C NMR, and IR spectra. The assignment of the signals in NMR spectra was done with the use of quantum-chemical calculations of chemical shifts performed by the density functional method. The structure of one among compounds synthesized, N-(m-hydroxybenzoylamino)-bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboxamide, was proved by X-ray diffraction analysis.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Grekov, A.P., Organicheskaya khimiya gidrazina (Hydrazine Organic Chemistry), Kiev: Tekhnika, 1966, 235 p.Google Scholar
  2. 2.
    Onishchenko, A.S., Dienovyi sintez (Diene Synthesis), Moscow: Izd. Akad. Nauk SSSR, 1963, 314 p.Google Scholar
  3. 3.
    US Patent 3277111, 1966; Ref. Zh. Khim., 1968, 6N729P.Google Scholar
  4. 4.
    Japan Patent 9319 1967; Ref. Zh. Khim., 1968, 21N595; Furdik, M., Sidoova, E., and Priechradny, S., Acta Fac. Rerum. Nature. Univ. Com. Chim., 1968, vol. 12, p. 253; Japan Patent 59-122465, 1984; Ref. Zh. Khim., 1985, 15O39P; Koval, I., Sulfur Reports, 1993, vol. 14, p. 149.Google Scholar
  5. 5.
    Japan Patent 48-2552, 1973; Ref. Zh. Khim., 1973, 23N365P.Google Scholar
  6. 6.
    German Patent 295630 1991; Ref. Zh. Khim., 1992, 18O149P.Google Scholar
  7. 7.
    Kas'yan, A.O., Krishchik, O.V., Krasnovskaya, O.Yu., and Kas'yan, L.I., Zh. Org. Khim., 1998, vol. 34, p. 1802.Google Scholar
  8. 8.
    Kas'yan, L.I., Krishchik, O.V., Umrykhina, L.K., and Kas'yan, A.O., Vestn. DGU, Khimiya, 1998, p. 87.Google Scholar
  9. 9.
    Nakanisi, K., Infrakrasnye spektry organicheskikh molekul (IR Spectra of Organic Molecules), Moscow: Mir, 1965, 209 p.Google Scholar
  10. 10.
    Keith, T.A. and Bader, R.F.W., Chem. Phys. Lett., 1992, vol. 194, p. 1; Keith, T.A. and Bader, R.F.W., Can. J. Chem., 1996, vol. 74, p. 185.Google Scholar
  11. 11.
    Ditchfield, R., Mol. Phys., 1974, vol. 27, p. 789; Wolinski, K., Hilton, J.F., and Pulay, P.J., J. Am. Chem. Soc., 1990, vol. 112, p. 8251.Google Scholar
  12. 12.
    Rossikhin, V.V., Okovytyy, S.I., Kasyan, L.I., Voronkov, E.O., Umrikhina, L.K., and Leszczynski, J., J. Phys. Chem., 2002, vol 106, p. 4176.Google Scholar
  13. 13.
    Shustov, G.V., Dokl. Akad. Nauk SSSR, 1985, p. 1378.Google Scholar
  14. 14.
    Burgi, H.-B. and Dunitz, J.D., Structure Correlation, 1994, vol. 2, p. 741.Google Scholar
  15. 15.
    Kasyan, L.I., Zh. Org. Khim., 1999, vol. 35, p. 661.Google Scholar
  16. 16.
    Sheldrick, G.M., SHELX97 PC, Version A. System of computer programs for the crystal structure solution and refinement, Rev. 2, 1998.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • O. V. Krishchik
    • 1
  • I. N. Tarabara
    • 1
  • A. O. Kas'yan
    • 2
  • S. V. Shishkina
    • 3
  • O. V. Shishkin
    • 3
  • A. K. Isaev
    • 1
  • L.I. Kas'yan
    • 1
  1. 1.Dnepropetrovsk National University DnepropetrovskUkraine
  2. 2.Organisch-chemische Institut von Rhein-Westfaelische UniversitaetAachen, BRD
  3. 3.Institute of Single crystalsKharkovUkraine

Personalised recommendations