BF3-H2O catalyzed Fries rearrangement of phenolic esters

Catalysis Letters

Volumn 114, Issue 1-2, 2007, Pages 24-29

  Prakash, G K Surya ^a   Panja, Chiradeep ^a   Mathew, Thomas ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

BF3 monohydrate; Fries rearrangement; Hydroxyketones; Para selectivity; Phenolic esters

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; KETONES; PHENOLS;

FRIES REARRANGEMENT; HYDROXYKETONES; PARA SELECTIVITY; PHENOLIC ESTERS;

ESTERS;

EID: 34247633521     PISSN: 1011372X     EISSN: 1572879X     Source Type: Journal    
DOI: 10.1007/s10562-007-9033-9     Document Type: Article

References (58)

1. (a) J. March, Advanced Organic Chemistry, 5th ed. (Wiley, New York, 2001) p. 725. (For reviews see:
2. (b) H.J. Shine, Aromatic Rearrangements (American Elsevier, New York, 1967) pp. 72-82, 365-368.
3. (c) A. Gerecs, in Friedel-Crafts and Related Reactions, Vol. III, ed. G.A. Olah (Intel-science, New York, 1964) p. 499.
4. (d) R. Martin, Org. Prep. Proced. Int. 24 (1992) 369 and references there in.
5. J. D'Ans and H. Limmer, Her. 85 (1952) 585.
6. (a) M.B. Knowles, US (1956) 2763691.
7. (b) H.R. Synder and C.T. Elston, J. Am. Chem. Soc. 77 (1955) 364.
8. (c) F. Effenberger and R. Gutmann, Chem. Ber. 115 (1982) 1089.
9. (d) O. Darm and A. Wylius, Justus Liebigs Ann. Chem. 587 (1954) 1.
10. (e) A. Commarieu, W. Hoelderich, J.A. Laffitte and M.P. Dupont, J. Mol. Catal. A: Chem. 182 (2002) 137.
11. (f) T. Ollevier, V. Desyroy, M. Asim and M.-C. Brochu, Synlett (2004) 2794 and references therein.
12. (a) G. Kuriakose, J.B. Nagy and N. Nagaraju, Stud. Surf. Sci. Catal. 154C (2004) 2803.
13. (b) C.S. Cundy, R. Higgins, S.A.M. Kibby, B.M. Lowe and R.M. Paton, Tetrahedron Lett. 30 (1989) 2281.
14. G.A. Olah, M. Arvanaghi and V.V. Krishnamurthy, J. Org. Chem. 48 (1983) 3359.
15. (a) E.F. Kozhevnikova, E.G. Derouane and I.V. Kozhevnikova, Chcm. Commun. (2002) 1178.
16. (b) M. Misono, Chem. Commun. (2001) 1141.
17. (c) R.V. Gricken, J.A Melero and G. Morales, Appl. Catal. A: Gen. 289 (2005) 143.
18. (a) C.R. Hauser and E.H. Man, J. Org. Chem. 17 (1952) 390.
19. (b) R. Baltzly, W.S. Ide, and A.P. Phillips, J. Am. Chem. Soc. 77 (1955) 2522.
20. (c) Y. Ogata and H. Tabuchi, Tetrahedron 20 (1964) 1661.
21. (d) F. Krausz and R. Martin, Bull. Soc. Chim. Fr. (1965) 2192.
22. (e) R. Martin, Bull. Soc. Chim. Fr. (1974) 11-983.
23. (f) A. Warshawsky, R. Kalir, A. Patchornik, J. Am. Chem. Soc. 100 (1978) 4544.
24. (g) R. Martin, Bull. Soc. Chim. Fr. (1979) 11-373.
25. (h) J.L. Dowson, J.L. Gibson, L.S. Hart, C.R. Waddington, J. Chem. Soc. Perkin Trans. 2 (1989) 2133.
26. (i) J.L. Gibson, L.S. Hart, J. Chem. Soc. Perkin Trans. 2 (1991) 1343.
27. (j) A.M.A.G. Oliveira, A.M.F. Oliveira-Compas, M.M.M. Raposo, J. Griffiths, A.E.H. Machado, Tetrahedron 60 (2004) 6145.
28. (k) A.B. Bagno, W. Kantlehner, R. Kress, G. Saielli and E. Stoyanov, J. Org. Chem. ASAP (2006).
29. (a) D. Belluš and P. Hrdlovié, Chem. Rev. 67 (1967) 599.
30. (b) T.J. Dickerson, M.R. Tremblay, T.Z. Hoffman, D.I. Ruiz, and K.D. Janda, J. Am. Chem. Soc. 125 (2003) 15395.
31. (c) W. Gu and R.G. Weiss, J. Org. Chem. 66 (2001) 1775.
32. (c) L.K. Crevatín, S.M. Bonesi and R. Erra-Balsells, Helv. Chim. Acta 89 (2006) 1147.
33. (a) H. Sharghi and Z. Shahsavari-Fard, Phosphorus, Sulfur Silicon Relat. Elem. 180 (2005) 2491.
34. (b) T.K. Pradhan, A. De and J. Mortier, Tetrahedron 38 (2005) 61.
35. (c) X. Chen, M. Tordeux, J.-R. Desmurs and C. Wakselman, J. Fluorine. Chem. 123 (2003) 51.
36. (d) F.M. Moghaddam, M.G. Dekamin and M. Ghaffarzadeh, Tetrahedron Lett. 42 (2001) 8119.
37. (e) M.E. Jung and T.I. Lazarova, Tetrahedron Lett. 37 (1996) 7.
38. (d) Z. Zhao, J. Messinger, U. Schoen, R. Wartchow and H. Butenschoen, Chem. Commun. (2006) 3007.
39. (a) K.P. Jayasundera, A.J. Watson and C.M. Taylor, Tetrahedron Lett. 46 (2005) 4311.
40. (b) C.M. Taylor and A.J. Watson, Curr. Org. Chem. 8 (2004) 623.
41. (c) K.P. Jayasundera, A.J. Watson and C.M. Taylor, Tetrahedron Lett. 46 (2005) 4311.
42. (a) M. Easwaramurthy, R. Ravikumar, A.J. Lakshmanan, and G.J. Raju, Indian J. Chem.: Section B: Org. Chem. Incl. Med. Chem. 44B (2005) 635.
43. (b) H. Kobasa, J. Org. Chem. 27 (1962) 2293.
44. (c) D.A. Plank, Tetrahedron Lett. 52 (1968) 5423.
45. (a) J.-J. Lee, C.-B. Kim, S.-M. Park, B.-C. Lee and H.-B. Pyo, WO (2005) 2005054169.
46. (b) V. Borzatta, E. Poluzzi and A. Vaccari, WO (2001) 2001023339.
47. (c) P. Hope and J. Gray, US (1973) 1470665.
48. G. Effenberger, Chem. Ber. 115 (1982) 1089.
49. H. Meerwein, Chem. Ber. 66 (1933) 411.
50. (a) K. Kindler and H. Oelschlager, Chem. Ber. 87 (1954) 194.
51. (b) J.L. Boyer, J.E. Krum, M.C. Myers, A.N. Fazal and C.T. Wigal, J. Org. Chem. 65 (2000) 4712.
52. D. Fãrcasiu and A. Ghenciu, J. Catal. 134 (1992) 126.
53. (a) G.A. Olah, Q. Wang, X.-Y. Li and I. Bucci, Synthesis (1992) 1085.
54. (b) G.A. Olah, Q. Wang, N. Trivedi and G.K.S. Prakash, Synthesis (1992) 465.
55. (c) G.A. Olah, Q. Wang and G.K.S. Prakash, Catal. Lett. 13 (1992) 55.
56. (d) O.A., Olah, Q. Wang, X.-Y. Li and G.K.S. Prakash, Synlett (1993) 32.
57. (e) G.A. Olah, Q. Wang, X.-Y. Li and G.K.S. Prakash, Synthesis (1993) 207.
58. (f) G.K.S. Prakash, T. Mathew, D. Hoole, P.M. Esteves, Q. Wang, G. Rasul and G.A. Olah, J. Am. Chem. Soc. 126 (2004) 15770.