Part of the book series: NATO ASI Series ((ASIC,volume 165))

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Abstract

Ene-reactions occur generally at high temperature. Lewis acid catalysis allows ene-reactions under mild conditions. The ene-reaction of diethyloxomalonate, which is a very reactive enophile with olefins is catalyzed by kaolin, montmorillonite or H+ doped montmorillonite. The ene-reaction products are converted into γ-lactones, especially by acidic montmorillonite. The conversion of citronellal into isopulegol is catalyzed by montmorillonite.

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References

  1. - B.K.C. Theng, ‘The Chemistry of Clay-Organic Reactions’, Hilger, London, 1974.

    Google Scholar 

  2. - J.M. Thomas, ‘Intercalation Chemistry’, M.S. Whittingham and A.J. Jacobson, Ed. Academic Press, New York, 1982, chapter 3.

    Google Scholar 

  3. - M. Frenkel and L. Heller Kallai, Clays and Clay mineral, 31, 92 (1983).

    Article  CAS  Google Scholar 

  4. - E.C. Taylor and C.S. Chiang, Synthesis, 467 (1977). V.M. Thuy and P. Maitte, Bull. Soc. Chim. Fr., 264 (1978).

    Google Scholar 

  5. - A. Cornelis, P. Laszlo and P. Pennetreau, Clay Miner. 18, 437 (1983) and cited references.

    Article  CAS  Google Scholar 

  6. - P. Laszlo and J. Luchetti, Tetrahedron Lett., 25, 1567, 2147 (1984).

    Google Scholar 

  7. - H.M.R. Hoffmann, Angew Chem. Int. Ed. Engl. 8, 556 (1969). W. Oppolzer and V. Snieckus, Angew. Chem. Int. Ed. Engl. 17, 476 (1978). J.M. Conia and P. Le Perchec, Synthesis, 1 (1975).

    Google Scholar 

  8. - B.B. Snider, Acc. Chem. Res. 13, 426 (1980).

    Article  CAS  Google Scholar 

  9. - K.H. Schulte-Elte and G. Ohloff, Helv. Chim. Acta, 21, 153 (1967).

    Article  Google Scholar 

  10. - Y. Nakatani and K. Kawashima, Synthesis, 147 (1978).

    Google Scholar 

  11. - M.F. Salomon, S.N. Pardo and R.G. Salomon, J. Am. Chem. Soc. (a) 102, 2473 (1980) (b) 106, 3797 (1984).

    Google Scholar 

  12. - M.F. Salomon, S.N. Pardo and R.G. Salomon, J. Org. Chem., 49, 2446 (1984).

    Article  CAS  Google Scholar 

  13. - R.H. Wightman, J. Chem. Soc. Chem. Comm., 818 (1979).

    Google Scholar 

  14. - M. Frenkel, ‘Clays and Clay Minerals’, 22, 435 (1974).

    Article  CAS  Google Scholar 

  15. - S.S. Cady and T.J. Pinnavaia, Inorg. Chem. 17, 1501 (1978).

    Article  CAS  Google Scholar 

  16. - J.M. Adams, D.E. Clement and S.H. Graham, Clays and Clay Minerals, 31, 129 (1983).

    Article  CAS  Google Scholar 

  17. - A. Foucaud and D. Saib, unpublished observations.

    Google Scholar 

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© 1986 D. Reidel Publishing Company, Dordrecht, Holland

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Roudier, J.F., Foucaud, A. (1986). Clay Catalyzed Ene-Reactions. Synthesis of γ-Lactones. In: Setton, R. (eds) Chemical Reactions in Organic and Inorganic Constrained Systems. NATO ASI Series, vol 165. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-4582-1_18

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  • DOI: https://doi.org/10.1007/978-94-009-4582-1_18

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-8536-6

  • Online ISBN: 978-94-009-4582-1

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