Chemical Transformation of 1,8-Cineole. Synthesis of N-Phenylimides from Cineolic Acid

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

Armando J. D. Silvestre, José A. S. Cavaleiro, Artur M. S. Silva, Bernard Delmond and Claude Filliatre


Abstract

Chemical transformations of 1,8-cineole into cineolic acid derivatives, including N-phenylimides 6, are reported; based on spectroscopic data the regioselectivity of some of the reactions and the heterocyclic ring conformation for each group of compounds have been established.


References

  1. I. D. Rae and A. M. Rewood, Aust. J. Chem., 1974, 1143 CAS.
  2. A. J. D. Silvestre, J. A. S. Cavaleiro, A. M. S. Silva, B. Delmond and C. Filliatre, Heterocycl. Commun., 1996, 2, 371 Search PubMed.
  3. A. J. D. Silvestre, J. A. S. Cavaleiro, B. Delmond, C. Filliatre and G. Bourgeois, Flavour Fragrance J., 1994, 9, 51 Search PubMed.
  4. A. J. D. Silvestre, J. A. S. Cavaleiro, B. Delmond, C. Filliatre and G. Bourgeois, Industrial Crops and Products, 1997, 6, 27 Search PubMed.
  5. J. A. S. Cavaleiro, G. M. S. F. C. Nascimento, M. G. M. S. Neves, M. T. Pinto, A. J. D. Silvetre and M. G. H. Vicente, Tetrahedron Lett., 1996, 37, 1893 CrossRef CAS.
  6. A. C. Tomé., J. A. S. Cavaleiro, F. M. J. Domingues and R. J. Cremlyn, Phosphorus Sulphur Silicon Relat. Elem., 1993, 79, 187 Search PubMed.
  7. M. Hargreaves, J. Pritchard and H. Dave, Chem. Rev., 1970, 70, 439 CrossRef CAS.
  8. D. Tanner and P. Somfai, Tetrahedron, 1988, 44, 613, 619.
  9. K. Venkataraman and D. R. Wagle, Tetrahedron Lett., 1979, 32, 3037 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.