View PDF Version
 
DOI: 10.1039/A902759I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 2609-2614

Reactivity of 4-R-1,2,4-triazoline-3,5-diones towards nitrone spin-traps: spectral study of the reaction with 5,5-dimethylpyrroline-N-oxide

(Note: The full text of this document is currently only available in the PDF Version )

Ana-Maria Alstanei, Florence Risi, Micheline Carles, Jean-Pierre Aycard, Louis Pizzala and Elena Volanschi

Abstract

Previous studies of the reactivity of 4-R-1,3,4-triazoline-3,5-diones (R = CH3, C6H5) have shown that, when 5,5-dimethylpyrroline-N-oxide (DMPO) is used as a spin-trap, a thermal reaction between the dione and the spin-trap occurs, leading to the same spin-adduct as by proper spin-trapping. Therefore, the reaction between two 4-R-triazolinediones (RTAD) with DMPO was investigated by combined spectral methods, including UV–Visible, FT-IR, 1H and 13C NMR and EPR spectroscopy. The results were rationalised in terms of a reaction sequence in which the spin-adduct is formed via a modified version of the Forrester–Hepburn mechanism and the rate determining step is the oxidation of the spin-adduct by RTAD, leading to the final product.

References

  1. F. Risi, A. M. Alstanei, E. Volanschi, M. Carles, L. Pizzala and J. P. Aycard, J. Org. Chem., submitted Search PubMed.
  2. R. Briere and A. Rassat, Tetrahedron, 1976, 32, 2891 CrossRef CAS.
  3. W. H. Pirkle and P. L. Gravel, J. Org. Chem., 1978, 43, 808 CrossRef CAS.
  4. A. M. Alstanei, PhD thesis, University of Bucharest, 1998; F. Risi, PhD thesis, University of Provence, 1998.
  5. T. Matsuoka and K. Harano, Tetrahedron, 1995, 51, 6451 CrossRef CAS and refs. therein.
  6. L. Eberson, J. Chem. Soc., Perkin Trans. 2, 1994, 171 RSC.
  7. J. Forrester and E. Hepburn, J. Chem. Soc., 1971, 701 Search PubMed.
  8. E. G. Janzen and I. Ping-Liu, J. Magn. Reson., 1973, 9, 510 CAS.
  9. L. Eberson, J. J. MacCullogh and O. Persson, J. Chem. Soc., Perkin Trans. 2, 1997, 133 RSC.
  10. L. Eberson, M. P. Hartshorn and O. Persson, J. Chem. Soc., Perkin Trans. 2, 1997, 195 RSC.
  11. P. Carloni, L. Eberson, L. Greci, P. Sgarabotti and P. Stippa, J. Chem. Soc., Perkin Trans. 2, 1996, 1297 RSC.
  12. M. J. Bausch and B. David, J. Org. Chem., 1992, 57, 1118 CrossRef CAS.
  13. L. Eberson, Electron Transfer in Organic Chemistry, Springer Verlag, 1987 Search PubMed.
  14. L. Eberson and O. Persson, J. Chem. Soc., Perkin Trans. 2, 1997, 1689 RSC.
  15. S. Mallakpour, J. Chem. Educ., 1992, 69, 238 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.