Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono-and dibromide derivatives: Unexpected Wagner-Meerwein rearrangement on silica gel

Turkish Journal of Chemistry

Volumn 35, Issue 4, 2011, Pages 587-598

  Eşsiz, Selçuk ^a   Şengül, Mehmet Emin ^a   Şahin, Ertan ^a   Daştan, Arif ^a  

^a ATATÜRK UNIVERSITY   (Turkey)

Author keywords

Benzobarrelene; Bromination; Wagner Meerwein rearrangement

Indexed keywords

EID: 79960233091     PISSN: 13000527     EISSN: 13036130     Source Type: Journal    
DOI: 10.3906/kim-1101-991     Document Type: Article

References (34)

1. Pongkittiphan, V.; Theodorakis, E. A.; Chavasiri, W. Tetrahedron Lett. 2009, 50, 5080-5082.
2. Borsato, G.; Brussolo, S.; Crisma, M.; De Lucchi, O.; Lucchini, V.; Zambon, A. Synlett 2005, 1125-1128.
3. Borsato, G.; De Lucchi, O.; Fabris, F.; Groppo, L.; Lucchini, V.; Zambon, A. J. Org. Chem. 2002, 67, 7894-7897.
4. Borsato, G.; De Lucchi, O.; Fabris, F.; Lucchini, V.; Pasqualotti, M.; Zambon, A. Tetrahedron Lett. 2003, 44, 561-563.
5. Cossu, S.; Cimenti, C.; Peluso, P.; Paulon, A.; De Lucchi, O. Angew. Chem. Int. Edit. 2001, 40, 4086-4089.
6. Dalkilic, E.; Guney, M.; Dastan, A.; Saracoglu, N.; De Lucchi, O.; Fabris, F. Tetrahedron Lett. 2009, 50, 1989-1991.
7. Dastan, A.; Fabris, F.; De Lucchi, O.; Guney, M.; Balci, M. Helv. Chim. Acta 2003, 86, 3411-3416.
8. De Lucchi, O.; Dastan, A.; Altundas, A.; Fabris, F.; Balci, M. Helv. Chim. Acta 2004, 87, 2364-2367.
9. Durr, R.; Cossu, S.; Lucchini, V.; De Lucchi, O. Angew. Chem. Int. Edit. 1997, 36, 2805-2807.
10. Fabris, F.; Bellotto, L.; De Lucchi, O. Tetrahedron Lett. 2003, 44, 1211-1213.
11. Fabris, F.; Pellizzaro, L.; Zonta, C.; De Lucchi, O. Eur. J. Org. Chem. 2007, 283-291.
12. Padovan, P.; Tartaggia, S.; Lorenzon, S.; Rosso, E.; Zonta, C.; De Lucchi, O.; Fabris, F. Tetrahedron Lett. 2009, 50, 1973-1976.
13. Zonta, C.; Cossu, S.; De Lucchi, O. Eur. J. Org. Chem. 2000, 1965-1971.
14. Zonta, C.; De Lucchi, O.; Linden, A.; Lutz, M. Molecules 2010, 15, 226-232.
15. Zonta, C.; Fabris, F.; De Lucchi, O. Org. Lett. 2005, 7, 1003-1006.
16. Adam, W.; Balci, M.; Cakmak, O.; Peters, K.; Saha-Möller, C. R.; Schulz, M. Tetrahedron 1994, 50, 9009-9012.
17. Adam, W.; Ahrweiler, M.; Balci, M.; Cakmak, O.; Saha-Möller, C. R. Tetrahedron Lett. 1995, 36, 1429-1430.
18. Altundas, R.; Balci, M. Tetrahedron 1993, 49, 6521-6526.
19. Laird, D. W.; Gilbert, J. C. J. Am. Chem. Soc. 2001, 123, 6704-6705.
20. Tumer, F.; Taskesenligil, Y.; Balci, M. J. Org. Chem. 2001, 66, 3806-3810.
21. De La Mare, P. B. D.; Bolton, R. In Electrophilic Additions to Unsaturated Systems, 2nd ed., Elsevier, New York, 1982.
22. Lobanova, T. P.; Berus, E. I.; Barkhash, V. A. Zh. Obshch. Khim. 1969, 39, 2332 (Chemical Abstract Number: 72:43270).
23. Dastan, A.; Balci, M. Tetrahedron 2005, 61, 5481-5488.
24. Gultekin, D. D.; Taskesenligil, Y.; Dastan, A.; Balci, M. Tetrahedron 2008, 64, 4377-4383.
25. Sengul, M. E.; Gultekin, D. D.; Essiz, S.; Dastan, A. Turk. J. Chem. 2009, 33, 79-86.
26. Sengul, M. E.; Gultekin, D. D.; Essiz, S.; Sahin, E.; Dastan, A. Tetrahedron 2009, 65, 4859-4865.
27. Taskesenlioglu, S.; Dastan, A.; Dalkilic, E.; Guney, M.; Abbasoglu, R. New J. Chem. 2010, 34, 141-150.
28. Smith, W. B.; Saint, C.; Johnson, L. R. J. Org. Chem. 1984, 49, 3771-3774.
29. Povolotskaya, N. N.; Limasova, T. I.; Berus, E. I.; Exner, O.; Barkhash, V. A. J. Org. Chem. USSR (Engl. Transl.) 1970, 6, 1615.
30. Hill, R. K.; Pendalwar, S. L.; Kielbasinski, K.; Baevsky, M. F.; Nugara, P. N. Synth. Commun. 1990, 20, 1877.
31. Dastan, A. Tetrahedron 2001, 57, 8725-8732.
32. Winstein, S. J. Am. Chem. Soc. 1961, 83, 1516-1517.
33. Rigaku/MSC, Inc., 9009 New Trails Drive, The Woodlands, TX 77381, USA.
34. Sheldrick, G. M. SHELXS97 and SHELXL97, University of Göttingen, Germany, 1997.