7-Oxabicyclo[2.2.1]heptadiene derivatives: reactivity towards Brønsted acids

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Alain Maggiani, Arlette Tubul and Pierre Brun


Abstract

7-Oxabicyclo[2.2.1]heptadiene derivatives can be converted to phenols, fulvenes and/or the products from a retro-Diels–Alder-like reaction by treatment with Brønsted acids; the outcome of the reaction depends on the experimental conditions and the nature of the Brønsted acid used.


References

  1. A. Maggiani, A. Tubul and P. Brun, Synthesis, 1997, 631 CrossRef CAS.
  2. R. D. Little and G. N. Muller, J. Am. Chem. Soc., 1981, 103, 2744 CrossRef CAS.
  3. R. D. Little, G. L. Caroll and J. L. Petersen, J. Am. Chem. Soc., 1983, 105, 928 CrossRef CAS.
  4. A. Maggiani, A. Tubul and P. Brun, Tetrahedron Lett., 1998, 39, 4485 CrossRef CAS.
  5. P. Vogel, B. Willhalm and H. Prinzbach, Helv. Chim. Acta, 1969, 52, 584 CAS.
  6. D. S. Stusche and H. Prinzbach, Chem. Ber., 1973, 106, 3817 CAS.
  7. A. Bruggink, H. Hogeveenh and T. B. Middlekoop, Tetrahedron Lett., 1972, 4961 CrossRef CAS.
  8. R. K. Bansal, A. W. McCulloch, P. W. Rasmussen and A. G. McInnes, Can. J. Chem., 1975, 53, 138 CAS.
  9. General procedure for the retro-DA reaction induced by anhydrous HCl: a stirred solution of the oxabicyclic derivative 1 in CH2Cl2(0.5 ml per 0.1 mmol of substrate) was saturated with anhydrous HCl (between 1.5 and 2 h). The solution was stirred at room temperature for 48 h. The solution was washed with water to neutrality. The organic layer was dried over MgSO4 and then concentrated under vacuum. The crude product was purified by flash chromatography (eluent: hexane–Et2O).
  10. R. Bloch and G. Mandville, Novel strategies for the use of retro-Diels–Alder reactions in stereoselective synthesis, in Recent research developments in organic chemistry, ed. S. G. Pandalai, TRN, Trivadrum, India, 1998, vol. 2, pp. 411-452 Search PubMed.
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