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Chemistry of Heterocyclic Compounds

, Volume 40, Issue 12, pp 1618–1625 | Cite as

Study of reaction of 5-aryl-2,3-dihydro-2,3-furandiones with n-cyanotriphenylphosphinimine. Molecular and crystal structure of the solvate of 6-p-tolyl-2-triphenylphosphinimino-4H-1,3-oxazin-4-one with acetonitrile

  • D. D. Nekrasov
  • S. N. Shurov
  • Yu. T. Struchkov
Article

Abstract

We have used X-ray diffraction to establish the structure of 6-p-tolyl-2-triphenylphosphinimino-4H-1,3-oxazin-4-one. We have modeled its formation from 5-p-toluoylketene and N-cyanotriphenylphosphinimine using the semiempirical SCF MO LCAO method in the MNDO-PM3 approximation. We show that the reaction occurs according to a concerted mechanism.

Keywords

5-aryl-2,3-dihydro-2,3-furandiones 6-aryl-2-triphenylphosphinimino-4H-1,3-oxazin-4-ones aroylketenes N-cyanotriphenylphosphinimine transition state semiempirical SCF MO LCAO method X-ray diffraction 

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REFERENCES

  1. 1.
    D. D. Nekrasov, Yu. S. Andreichikov, and O. A. Rakitin, Zh. Org. Khim., 28, 1319 (1992).Google Scholar
  2. 2.
    A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, and R. Taylor, J. Chem. Soc., Dalton Trans., 83 (1989).Google Scholar
  3. 3.
    A. N. Chernega, A. A. Korkin, M. Yu. Antipin, and Yu. T. Struchkov, Zh. Obshch. Khim., 9, 2045 (1988).Google Scholar
  4. 4.
    F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1 (1987).Google Scholar
  5. 5.
    E. Bayer and G. Hofelinger, Chem. Ber., 99, 1 689 (1966).Google Scholar
  6. 6.
    Yu. S. Andreichikov, Yu. A. Nalimova, A. P. Kozlov, and I. A. Rusakov, Zh. Org. Khim., 14, 2436 (1978).Google Scholar
  7. 7.
    Yu. S. Andreichikov, G. Kollenz, C. P. Kappe, R. Lueng-Toung, and C. Wentrup, Acta Chem. Scand., 46, 683 (1992).CrossRefGoogle Scholar
  8. 8.
    Yu. S. Andreichikov, S. N. Shurov, V. V. Zalesov, and N. N. Shapet’ko, Zh. Org. Khim., 22, 857 (1986).Google Scholar
  9. 9.
    M. J. P. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).Google Scholar
  10. 10.
    M. J. P. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).Google Scholar
  11. 11.
    J. J. P. Stewart, J. Comput. Chem., 10, 202 (1989).Google Scholar
  12. 12.
    Yu. S. Andreichikov and D. D. Nekrasov, Zh. Org. Khim., 20, 1755 (1984).Google Scholar
  13. 13.
    J. J. P. Stewart, MOPAC. Version 7.0, Frank J. Seiler Research Laboratory, US Air Force Academy, QCMP 175.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2004

Authors and Affiliations

  • D. D. Nekrasov
    • 1
  • S. N. Shurov
    • 1
  • Yu. T. Struchkov
    • 1
  1. 1.Perm State UniversityPermRussia

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