Selective palladium-catalysed functionalization of limonene: Synthetic and mechanistic aspects

Journal of Molecular Catalysis A: Chemical

Volumn 135, Issue 1, 1998, Pages 11-22

  El Firdoussi, Larbi ^a   Baqqa, Ahmed ^a   Allaoud, Smail ^a   Ait Allal, Badia ^a   Karim, Abdallah ^a   Castanet, Yves ^b   Mortreux, André ^b  

^a FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

^b CNRS   (France)

Author keywords

Acetoxylation; Allylic oxidation; Limonene; Methoxylation; Palladium

Indexed keywords

EID: 0032578437     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(97)00285-9     Document Type: Article

References (31)

1. J. Tsuji, Organic Synthesis with Palladium Compounds, Springer, New York, 1980.
2. B.M. Trost, T.R. Verhoeven, in: G. Wilkinson (Ed.), Comprehensive Organometallic Chemistry, Pergamon, Oxford, 1982, pp. 799-938.
3. A. Heumann, K.J. Jens, M. Reglier, in: K.D. Karlin (Eds.), Progress in Inorganic Chemistry, Vol. 42, 1994, p. 483.
4. Bäckvall J.E. Palladium in organic synthesis. Tetrahedron Symposia. 50:1994;285. in-print.
5. J. Tsuji, Palladium reagents, Innovation in Organic Synthesis, Wiley, New York, 1996.
6. J.E. Bäckvall, in: J. Streith, H. Prinzbach, G. Schill (Eds.), Organic Synthesis: An Interdisciplinary Challenge, Blackwell, Oxford, 1985 p. 69.
7. Bäckvall J.E., Vagberg J.O. J. Org. Chem. 53:1988;5695.
8. Hansson S., Heumann A., Rein T., Akermark B. J. Org. Chem. 55:1990;975.
9. H. Grennberg, V. Simon, J.E. Bäckvall, J. Chem. Soc., Chem. Comm., 1994, p. 265.
10. T.T. Wenzel, J. Chem. Soc., Chem. Commun., 1993, p. 862.
11. Muzart J. Bull. Soc. Chim. Fr. 1:1986;65.
12. Alper H., Harustiak M. J. Mol. Catal. 84:1993;87.
13. Heumann A., Réglier M., Waegell B. Angew. Chem., Suppl. Int. Ed. Engl. 21:1982;366.
14. N. Ferret, L.M. Mathieu, J.P. Zahra, B. Waegell, J. Chem. Soc., Chem. Commun., 1994, p. 2589.
15. Fdil N., Romane A., Allaoud S., Karim A., Castanet Y., Mortreux A. J. Mol. Catal. 108:1996;15.
16. Wilson J.W., Shaw P.E. J. Org. Chem. 38:1973;1684.
17. Chiaroni A., Riche C., El Firdoussi L., Benharref A., Karim A. Acta Crystallogr. C. 49:1993;365.
18. El Firdoussi L., Allaoud S., Karim A., Barrero A.F., Quirós M., Castanet Y., Mortreux A. Acta Crystallogr. C. 53:1997;710.
19. P. Teissere, Chimie des Substances Odorantes, Lavoisier, Paris, 1991.
20. El Firdoussi L., Benharref A., Allaoud S., Karim A., Castanet Y., Mortreux A., Petit F. J. Mol. Catal. 72:1992;L1.
21. Liu H.J., Nyangulu J.M. Tetrahedron Lett. 30:1989;5097.
22. Ranner K.D., Strauss C.R., Viskov F., Mokbel L. J. Org. Chem. 58:1993;950.
23. Backvall J.E., Byström S.E., Nordberg R.E. J. Org. Chem. 49:1984;4619.
24. Grennberg H., Gogoll A., Bäckvall J.E. Organometallics. 12:1993;1790.
25. Kitching W., Rappoport Z., Winstein S., Young W.G. J. Am. Chem. Soc. 88:1966;2054.
26. K. Dunne, F.J. McQuillin, J. Chem. Soc. C, 1970, pp. 2200.
27. Horiuchi C.A., Satoh J.Y. J. Organomet. Chem. C. 45:1983;258.
28. Wilhelm D., Bäckvall J.E., Nordberg R.E., Norin T. Organometallics. 4:1985;1296.
29. Tabor D.C., White F.H., Colier L.W., Evans S.A. J. Org. Chem. 48:1983;1643.
30. Hiramatsu M., Nakano H., Fujinami T., Sakai S. J. Organomet. Chem. 236:1982;131.
31. Bohlmann F., Zeisberg R. Org. Magnetic Resonance. 7:1975;426.