Bromination and iodination of 6H,12H-5, 11-methanodibenzo[b,f][1,5] diazocine: A convenient entry to unsymmetrical analogs of Tröger's base

European Journal of Organic Chemistry

Volumn , Issue 23, 2007, Pages 3905-3910

  Didier, Delphine ^a   Sergeyev, Sergey ^a  

^a UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

Bromination; Electrophilic substitution; Heterocycles; Iodination; Tr ger's base

Indexed keywords

EID: 34547744410     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700253     Document Type: Article

References (33)

1. a) M. Valík, R. M. Strongin, V. Král, Supramol. Chem. 2005, 17, 347-367;
2. b) B. Dolensky, J. Elguero, V. Král, C. Pardo, M. Valík, Adv. Heterocycl. Chem. 2007, 93, 1-56;
3. c) J. C. Adrian Jr, C. S. Wilcox, J. Am. Chem. Soc. 1992, 114, 1398-1403;
4. d) S. Paliwal, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497-4498;
5. e) F. Hof, D. M. Scofield, W. B. Schweizer, F. Diederich, Angew. Chem. Int. Ed. 2004, 43, 5056-5059;
6. f) S. Sergeyev, F. Diederich, Angew. Chem. Int. Ed. 2004, 43, 1738-1740.
7. a) J. Artacho, P. Nilsson, K.-E. Bergquist, O. F. Wendt, K. Wärnmark, Chem. Eur. J. 2006, 12, 2692-2701;
8. b) M. Havlik, V. Kral, B. Dolensky, Org. Lett. 2006, 8, 4867-4870;
9. c) T. Mas, C. Pardo, J. Elguero, Helv. Chim. Acta 2005, 88, 1199-1207.
10. I. Sucholeiki, V. Lynch, L. Phan, C. S. Wilcox, J. Org. Chem. 1988, 53, 98-104.
11. J. Jensen, K. Wärnmark, Synthesis 2001, 1873-1877.
12. A. Hansson, J. Jensen, O. F. Wendt, K. Wärnmark, Eur. J. Org. Chem. 2003, 3179-3188.
13. J. Jensen, M. Strozyk, K. Wärnmark, J. Heterocycl. Chem. 2003, 40, 373-375.
14. S. Sergeyev, M. Schär, P. Seiler, O. Lukoyanova, L. Echegoyen, F. Diederich, Chem. Eur. J. 2005, 11, 2284-2294.
15. D. Didier, S. Sergeyev, Tetrahedron 2007, 63, 3864-3869.
16. a) J. Jensen, M. Strozyk, K. Wärnmark, Synthesis 2002, 2761-2765;
17. b) U. Kiehne, A. Lützen, Synthesis 2004, 1687-1695.
18. S. P. Bew, L. Legentil, V. Scholier, S. V. Sharma, Chem. Commun. 2007, 389-391.
19. F. Hof, M. Schär, D. M. Scofield, F. Fischer, F. Diederich, S. Sergeyev, Helv. Chim. Acta 2005, 88, 2333-2344.
20. J. Jensen, J. Tejler, K. Wärnmark, J. Org. Chem. 2002, 67, 6008-6014.
21. T. H. Webb, C. S. Wilcox, J. Org. Chem. 1990, 55, 363-365.
22. K. Staub, G. A. Levina, S. Barlow, T. C. Kowalczyk, H. S. Lackritz, M. Barzoukas, A. Fort, S. R. Marder, J. Mater. Chem. 2003, 13, 825-833.
23. a) E. B. Merkushev, Synthesis 1988, 923-937;
24. b) J. R. Hanson, J. Chem. Res. 2006, 277-280.
25. a) K. Orito, T. Hatakeyama, M. Takeo, H. Suginome, Synthesis 1995, 1273-1277;
26. b) A. Bachki, F. Foubelo, M. Yus, Tetrahedron 1994, 50, 5139-5146.
27. W. W. Sy, Tetrahedron Lett. 1993, 34, 6223-6224.
28. R. Johnsson, A. Meijer, U. Ellervik, Tetrahedron 2005, 61, 11657-11663.
29. C. Monnereau, E. Blart, F. Odobel, Tetrahedron Lett. 2005, 46, 5421-5423.
30. a) D. J. Sinclair, M. S. Sherburn, J. Org. Chem. 2005, 70, 3730-3733;
31. b) A. Blaszczyk, M. Chadim, C. von Haenisch, M. Mayor, Eur. J. Org. Chem. 2006, 3809-3825.
32. A. Hansson, T. Wixe, K.-E. Bergquist, K. Wärnmark, Org. Lett. 2005, 7, 2019-2022.
33. F. C. Cooper, M. W. Partridge, J. Chem. Soc. 1955, 991-994.