Lanthanide(in) and Group IV metal triflate catalysed electrophilic nitration: 'nitrate capture' and the rôle of the metal centre t

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 8, 1999, Pages 867-871

  Waller, Francis J ^a,b   Barrett, Anthony G M ^a,b   Christopher Braddock, D ^a,b   Murray McKinnell, R ^a,b   Ramprasad, Dorai ^a,b  

^a AIR PRODUCTS AND CHEMICALS INC   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000604190     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809914f     Document Type: Article

References (55)

1. J. H. Forsberg, V. T. Spaziano, T. M. Balasubramanian, G. K. Liu, S. A. Kinsley, C. A. Duckworth, J. J. Poteruca, P. S. Brown and J. L. Miller, J. Org. Oient., 1987,52, 1017.
2. S. Kobayashi, Synlett, 1994,689.
3. (a) H. Ishitani and S. Kobayashi, Tetrahedron Lett., 1996, 37, 7357;
4. (b) I. E. Marko and G. R. Evans, Tetrahedron Lett., 1994,35, 2771;
5. T. Saito, M. Kawamura and J.-I. Nishimura, Tetrahedron Lett., 1997,38,3231.
6. A. Kawada, S. Mitamura and S. Kobayashi, Cliem. Commun., 1996, 183.
7. S. Kobayashi and S. Nagayama, J. Org. Client., 1997,62, 232.
8. (a) S. Kobayashi, I. Hachiya and Y. Yamanoi, Bull. Cliem. Soc. Jpn., 1994, 67, 2342;
9. (b) H. Aspinall, A. F. Browning, N. Greeves and P. Ravenscroft, Tetrahedron Lett., 1994,35,4639.
10. A. G. M. Barrett and D. C. Braddock, Client. Commun., 1997, 351.
11. (a) S. Matsubara, M. Yoshioka and K. Utîmoto, Client. Lett., 1994, 827;
12. (b) S. Kobayashi, I. Hachiya, T. Takahori, M. Araki and H. Ishitani, Tetrahedron Lett., 1992, 33, 6815;
13. P. E. Harrington and M. A. Kerr, Synlett, 1996,1047;
14. ((/) E. Keller and B. L. Ferinca, Synlett, 1997,842.
15. (a) M. Meguro, N. Asao and Y. Yamamoto, J. Cliem. Soc., Perkin Trans. 1, 1994, 2579;
16. (b) M. Chini, P. Crotti, L. Favero, F. Macchia and M. Pineschi, Tetrahedron Lett., 1994, 35, 433.
17. (a) T. Hanamoto, Y. Sugimoto, Y. Yokoyama and J. Inanaga, J. Org. Client., 1996, 61,4491;
18. (b) S.-C. H. Diana, K.-Y Sim and T.-P Loh, Synlett, 1996, 263;
19. S. Kobayashi, H. Ishitani and M. Ueno, Synlelt,l99T, 115.
20. (a) F. J. Waller, A. G. M. Barren, D. C. Braddock and D. Ramprasad, Client. Commun., 1997, 613;
21. (b) F. J. Waller, D. Ramprasad, A. G. M. Barren and D. C. Braddock, Catalysis of Organic Reactions, ed. F. E. Merkes, Marcel Dekker, New York, 1998, p. 289.
22. M. Ouertani, P. Girard and H. B. Kagan, Tetrahedron Lett., 1982, 23,4315.
23. B. M. Trost, Angcu: Client., Int. Ed Engl., 1995, 34, 259.
24. F. J. Waller, A. G. M. Barren, D. C. Braddock and D. Ramprasad, Tetrahedron Lett., 1998, 39, 1641.
25. (a) G. A. Olah, R. Malhotra and S. C. Narang, Nitration: Methods and Mechanisms, VCH, New York, 1989;
26. (b) C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd edn., Cornell University Press, Ithaca, New York, 1969.
27. (a) J. M. Harrowfield, D. L. Kepert, J. M. Patrick and A. H. White, Amt. J. Chem., 1983, 36, 483;
28. (b) A. Chatterjee, E. N. Maslen and K. J. Watson, Ada Crystajldgr., 1988, B44, 381.
29. (a) T. Kowall, F. Foclia, L. Helm and A. E. Merbach, Chem. Eur. J., 1996, 2, 285}
30. (b) B. P. Hay, Inorg. Client., 1991, 30, 2876 and references cited therein.
31. I. Abrahamer and Y. Marcus, Inorg. Chem., 1967, 6, 2103.
32. P. J. Breen and W. D. Horrocks Jr., Inorg. Chem., 1983,22, 536.
33. A. Fratiello, V. Kubo-Anderson, E. Bolanos, O. Chavez, J. Ortega, R. D. Perrigan, F. Reyes, L. Saenz, S. M. Stoll and T. Thompson, J. Solution Chem., 1996, 25, 345 and references cited therein.
34. C. Bonal, J.-P. Morel and N. Morel-Desrosiers, J. Chem. Soc., Faraday Trans., 1996, 92,4957.
35. H. Yokoyama and G. Johansson, Acta. Chem. Scand., 1990,44, 567.
36. B. Piriou and D. R. Svoronos, J. Less-Common Met., 1985, 112, 275.
37. K. Ishihara, Y. Ishida, S. Nakamura and H. Yamamoto, Synlett, 1997,758.
38. (a) R. J. Thomas, W. F. Anzilotti and G. F. Hennion, Ind. Eng. Chem., 1940, 32, 408;
39. (b) G. F. Hennion, U S. Patent, 1943, 2 314 212.
40. D. W. Amos, D. A. Baines and G. W. Flewett, Tetrahedron Lett., 1973,3191.
41. S. Dincturk and J. H. Ridd, J. Chem. Soc., Perkin Trans. 2, 1982, 961.
42. B. M. Gatehouse, S. E. Livingstone and R. S. Nyholm, J. Chem. Soc., 1957,4222.
43. D. H. Johnston and D. F. Shriver, Inorg. Chem., 1993,32, 1045.
44. A. B. P. Lever, E. Mantovani and B. S. Ramaswamy, Can. J. Chem., 1971,49, 1957 and references cited therein.
45. J. R. Ferraro, C. Cristallin! and I. Fox, J. Inorg. Nucl. Chem., 1967, 29, 139.
46. (a) H. Brintzinger and R. E. Hester, Inorg. Chem., 1966, 5, 980;
47. (b) R. E. Hester and W. E. L. Grossman, Inorg. Client., 1996, 5, 1308.
48. C. C. Addison, N. Logan, S. C. Wallwork and C. D. Garner, Quart. Rev., 1971,25,289.
49. A. Habenschuss and F. Spedding, J. Client. Phys., 1979,70,2797.
50. (a) I. Hachiya, M. Moriwaki and S. Kobayashi, Bull. Chem. Soc. Jpn., 1995,68,2053;
51. (b) S. Kobayashi, M. Moriwaki and I. Hachiya, Bull. Chem. Soc. Jpn., 1997,70, 267.
52. Handbook of Chemistry and Physics, 66th edn., ed. R. C. Weast, CRC Press Inc., 1985-1986.
53. A. G. M. Barren, D. C. Braddock, J. P. Henschke and E. R. Walker, J. Chem. Soc., Perkin Trans, l, following paper.
54. T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 1995,117,4570.
55. S. Répichet, C. Le Roux, J. Dubac and J.-R. Desmurs, Eur. J. Org. Chem., 1998,2743.