Rearrangement of epoxides to carbonyl compounds in the presence of reusable acidic zeolite catalysts under mild conditions

Catalysis Letters

Volumn 109, Issue 1-2, 2006, Pages 77-82

  Smith, Keith ^a   El Hiti, Gamal A ^a,b   Al Shamali, Mahmoud ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b Tanta University   (Egypt)

Author keywords

4 substituted styrene oxides; Carbonyl compounds; Epoxide; Rearrangement; Zeolites

Indexed keywords

ALDEHYDES; CATALYSIS; HEATING; SUBSTITUTION REACTIONS; ZEOLITES;

4-SUBSTITUTED STYRENE OXIDES; CARBONYL COMPOUNDS; EPOXIDE; REARRANGEMENT;

ETHERS;

EID: 33745835821     PISSN: 1011372X     EISSN: 1572879X     Source Type: Journal    
DOI: 10.1007/s10562-006-0060-8     Document Type: Article

References (51)

1. R.E. Parker and N.S. Isaacs, Chem. Rev. 59 (1959) 737.
2. A.S. Rao, S.K. Paknikar and J.G. Kirtane, Tetrahedron 39 (1983) 2323.
3. J.G. Smith, Synthesis (1984) 629.
4. J. March, Advanced Organic. Chemistry, (Wiley, New York, 1992) ch. 18.
5. B. Rickborn, in: Comprehensive Organic Synthesis, Vol. 3, eds. B.M. Trost and I. Fleming (Pergamon Press, New York, 1991) ch. 3.3, pp. 733.
6. B. Rickborn and R.M. Gerkin, J. Am. Chem. Soc. 90 (1968) 4193.
7. G. Stork and J.W. Schulenberg, J. Am. Chem. Soc. 84 (1962) 284.
8. E.L. Eliel and D.W. Delmonte, J. Am. Chem. Soc. 80 (1958) 1744.
9. H.O. House, J. Am. Chem. Soc. 77 (1955) 3070.
10. H.O. House, J. Am. Chem. Soc. 77 (1955) 5083.
11. Y.D. Vankar, R.K. Saksena and A. Bawa, Chem. Lett. (1989) 1241.
12. B. Rickborn and R.M. Gerkin, J. Am. Chem. Soc. 93 (1971) 1693.
13. S.M. Naqvi, J.P. Horwitz and R. Filler, J. Am. Chem. Soc. 79 (1957) 6283.
14. H.O. House, Org. Synth. Coll. Vol. IV (1973) 375.
15. S. Kulasegaram and R.J. Kulawiec, J. Org. Chem. 62 (1997) 6547.
16. B.C. Ranu and U. Jana, J. Org. Chem. 63 (1998) 8212.
17. I. Karamé, M.L. Tommasino and M. Lemaire, Tetrahedron Lett. 44 (2003) 7687.
18. A. Procopio, R. Dalpozzo, A. De Nino, M. Nardi, G. Sindona and A. Tagarelli, Synlett. (2004) 2633.
19. M. Banerjee, U.K. Roy, P. Sinha and S. Roy, J. Organomet. Chem. 690 (2005) 1422.
20. A.M. Anderson, J.M. Blazek, P. Garg, B.J. Payne and R.S. Mohan, Tetrahedron Lett. 41 (2000) 1527.
21. E. Ruiz-Hitzky and B. Casai, J. Catal. 92 (1985) 291.
22. G. Paparatto and G. Gregorio, Tetrahedron Lett. 29 (1988) 1471.
23. D. Brunel, M. Chamoumi, B. Chiche, A. Finiels, G. Gauthier, P. Geneste, P. Graffin, F. Marichez and P. Moreau, Stud. Surf. Sci. Catal. 52 (1989) 139.
24. M. Chamoumi, D. Brunel, P. Geneste, P. Moreau and J. Solofo, Stud. Surf. Sci. Catal. 59 (1991) 573.
25. S. Matsumoto, M. Nitta and K. Aomura, Bull. Chem. Soc. Jpn. 47 (1974) 1537.
26. K. Smith and G.A. El-Hiti, Curr. Org. Synth. 1 (2004) 253.
27. K. Smith, S.D. Roberts and G.A. El-Hiti, Org. Biomol. Chem. 1 (2003) 1552.
28. K. Smith, G.A. El-Hiti, A.J. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 1560.
29. K. Smith, G.A. El-Hiti, A.J. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 2321.
30. K. Smith, G.M. Ewart, G.A. El-Hiti and K.R. Randles, Org. Biomol. Chem. 2 (2004) 3150.
31. K. Smith, G.A. El-Hiti, M.E.W. Hammond, D. Bahzad, Z. Li and C. Siquet, J. Chem. Soc. Perkin Trans. 1 (2000) 2745.
32. K. Smith, M. Butters, W.E. Paget, D. Goubet, E. Fromentin and B. Nay, Green Chem. 1 (1999) 83.
33. K. Smith, T. Gibbins, R.W. Millar and R.P. Claridge, J. Chem. Soc., Perkin Trans. 1 (2000) 2753.
34. K. Smith, S. Almeer, S.J. Black and C. Peters, J. Mater. Chem. 12 (2002) 3285.
35. K. Smith and M. Al-Shamali, Proceedings of 12th International Zeolite Conference, Mater. Res. Soc., Warrendale Vol. II (1999) 1129.
36. R. Fuchs, J. Am. Chem. Soc. 78 (1956) 5612.
37. W.K. Anderson and T. Veysoglu, J. Org. Chem. 38 (1973) 2267.
38. Y. Yano, T. Okonogi, M. Sunaga and W. Tagaki, J. Chem. Soc., Chem. Commun. (1973) 527.
39. E.J. Corey and W. Oppolzer, J. Am. Chem. Soc. 86 (1964) 1899.
40. T.W. Bentley, R.V.H. Jones, A.H. Larder and S.J. Lock, J. Chem. Soc., Perkin Trans. 2 (1998) 1407.
41. I.A. Rivero, R. Somanathan and L.H. Hellberg, Org. Prep. Proced. Int. 24 (1992) 363.
42. N.C.J.E. Chesters, D. O'Hagan and R.J. Robins, J. Chem. Soc., Perkin Trans. 1 (1994) 1159.
43. H.M. Barentsen, A.B. Sieval and J. Cornelisse, Tetrahedron 51 (1995) 7495.
44. H. Chikashita, Y. Morita and K. Itoh, Synth. Commun. 17 (1987) 677.
45. L. De Luca, G. Giacomelli, S. Masala and A. Porcheddu, J. Org. Chem. 68 (2003) 4999.
46. K. Ito and H. Tanaka, Chem. Pharm. Bull. 25 (1977) 1732.
47. E. Sachon, T. Milcent, S. Sagan, O. Convert, G. Chassaing and S. Lavielle, Tetrahedron Lett. 43 (2002) 7485.
48. S. Kulasegaram and R.J. Kulawiec, J. Org. Chem. 62 (1997) 6547.
49. I. Fleming, R.S. Roberts and S.C. Smith, J. Chem. Soc. Perkin Trans. 1 (1998) 1215.
50. R.A.M. O'Ferrall and B.A. Murray, J. Chem. Soc. Perkin Trans. 2 (1994) 2461.
51. M.H. Ali and C.J. Wiggin, Synth. Commun. 31 (2001) 3383.