Cycloaddition vs. conjugative Michael-type addition of 2-ethoxy-3-morpholinobuta-1,3-diene with nitroolefins

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Gašper Marc, Patrizia Nitti, Giuliana Pitacco, Alessandro Pizzioli and Ennio Valentin


Abstract

The reactivity of the title dienamine towards conjugated nitroolefins has been investigated. With 1-nitrocyclopentene carbocyclic products largely predominated, whereas with 1-nitrocyclohexene only Michael-type products were formed. The behaviour of β-nitrostyrene was found to be dependent on the reaction conditions used.


References

  1. (a) D. Enders, O. Meyer and G. Raabe, Synthesis, 1992, 1242 CrossRef CAS; (b) D. Enders, O. Meyer and G. Raabe, Synthesis, 1994, 66 CrossRef CAS; (c) R. H. Schlessinger and T. R. R. Pettus, J. Org. Chem., 1994, 59, 3246 CrossRef CAS; (d) J. Barluenga, F. Aznar, A. Martin and J. T. Vásquez, J. Am. Chem. Soc., 1995, 117, 9419 CrossRef CAS; (e) J. Barluenga, F. Aznar, M. P. Cabal and C. Valdes, J. Chem. Soc., Perkin Trans. 1, 1990, 633 RSC; (f) J. Barluenga, F. Aznar, M. P. Cabal, F. H. Cano and M. C. Foces-Foces, J. Chem. Soc., Chem. Commun., 1988, 1247 RSC.
  2. D. Pocar, P. Trimarco, R. Destro, E. Ortoleva and M. Ballabio, Tetrahedron, 1984, 40, 3579 CrossRef CAS.
  3. (a) Nitroalkanes and Nitroalkenes in Synthesis, A. G. M. Barrett ed., Tetrahedron, 1990, 46, 7313 Search PubMed; (b) G. Rosini and R. Ballini, Synthesis, 1988, 833 CrossRef; (c) A. G. M. Barrett and G. G. Graboski, Chem. Rev., 1986, 86, 751 CrossRef CAS; (d) D. Seebach, E. V. Colvin, F. Lehr and T. Weller, Chimia, 1979, 33, 1 CAS.
  4. J. Quick and R. Jenkins, J. Org. Chem., 1978, 43, 2275 CrossRef CAS.
  5. D. A. Harris, J. Chem. Soc., 1950, 2247 Search PubMed.
  6. W. A. White and H. Weingarten, J. Org. Chem., 1967, 32, 213 CrossRef CAS.
  7. F. Johnson, L. G. Duquette, A. Whitehead and L. C. Dorman, Tetrahedron, 1974, 30, 3241 CrossRef CAS.
  8. F. Johnson, Chem. Rev., 1968, 68, 3759.
  9. H. Mazarguil and A. Lattes, Bull. Soc. Chim. France, 1969, 319 CAS.
  10. G. Pitacco, A. Pizzioli and E. Valentin, Synthesis, 1996, 242 CrossRef CAS.
  11. F. Felluga, P. Nitti, G. Pitacco and E. Valentin, Tetrahedron, 1989, 45, 5667 CrossRef CAS.
  12. (a)E. L. Eliel, S. H. Wilen and L. N. Mandel, Stereochemistry of Organic Compounds, Wiley & Sons, New York, 1994, p. 769; (b)p. 738 Search PubMed.
  13. J. A. Kresge and Y. Yin, Can. J. Chem., 1987, 65, 1753.
  14. E. J. Corey and H. Estreicher, Tetrahedron Lett., 1981, 22, 603 CrossRef CAS.
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