Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel
The bromination reaction of dihydrobenzobarrelene under different conditions was studied. The bromination reaction of dihydrobenzobarrelene with molecular bromine gave only a Wagner-Meerwein rearrangement product by aryl and alkyl migration. Its high-temperature bromination reaction resulted in the formation of normal addition products besides rearrangement products. The bromination reaction of the alkene with 1,2- dibromotetrachloroethane (DBTCE) gave a non-rearrangement product as the sole product. The synthesis and bromination reaction of 2-bromodihydrobenzobarrelene was also studied. An unexpected Wagner-Meerwein rearrangement was observed on silica gel during the column chromatography of isomeric tribromides. Herein, we report the results of the synthesis, and the X-ray crystal structures and the possible mechanism of processes are discussed.
Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel
The bromination reaction of dihydrobenzobarrelene under different conditions was studied. The bromination reaction of dihydrobenzobarrelene with molecular bromine gave only a Wagner-Meerwein rearrangement product by aryl and alkyl migration. Its high-temperature bromination reaction resulted in the formation of normal addition products besides rearrangement products. The bromination reaction of the alkene with 1,2- dibromotetrachloroethane (DBTCE) gave a non-rearrangement product as the sole product. The synthesis and bromination reaction of 2-bromodihydrobenzobarrelene was also studied. An unexpected Wagner-Meerwein rearrangement was observed on silica gel during the column chromatography of isomeric tribromides. Herein, we report the results of the synthesis, and the X-ray crystal structures and the possible mechanism of processes are discussed.
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- Pongkittiphan, V.; Theodorakis, E. A.; Chavasiri, W. Tetrahedron Lett. 2009, 50, 5080-5082.
- Borsato, G.; Brussolo, S.; Crisma, M.; De Lucchi, O.; Lucchini, V.; Zambon, A. Synlett 2005, 1125-1128.
- Borsato, G.; De Lucchi, O.; Fabris, F.; Groppo, L.; Lucchini, V.; Zambon, A. J. Org. Chem. 2002, 67, 7894-7897.
- Borsato, G.; De Lucchi, O.; Fabris, F.; Lucchini, V.; Pasqualotti, M.; Zambon, A. Tetrahedron Lett. 2003, 44, 563.
- Cossu, S.; Cimenti, C.; Peluso, P.; Paulon, A.; De Lucchi, O. Angew. Chem. Int. Edit. 2001, 40, 4086-4089.
- Dalkilic, E.; Guney, M.; Dastan, A.; Saracoglu, N.; De Lucchi, O.; Fabris, F. Tetrahedron Lett. 2009, 50, 1989-1991.
- Dastan, A.; Fabris, F.; De Lucchi, O.; Guney, M.; Balci, M. Helv. Chim. Acta 2003, 86, 3411-3416.
- De Lucchi, O.; Dastan, A.; Altundas, A.; Fabris, F.; Balci, M. Helv. Chim. Acta 2004, 87, 2364-2367.
- Durr, R.; Cossu, S.; Lucchini, V.; De Lucchi, O. Angew. Chem. Int. Edit. 1997, 36, 2805-2807.
- Fabris, F.; Bellotto, L.; De Lucchi, O. Tetrahedron Lett. 2003, 44, 1211-1213.
- Fabris, F.; Pellizzaro, L.; Zonta, C.; De Lucchi, O. Eur. J. Org. Chem. 2007, 283-291.
- Padovan, P.; Tartaggia, S.; Lorenzon, S.; Rosso, E.; Zonta, C.; De Lucchi, O.; Fabris, F. Tetrahedron Lett. 2009, , 1973-1976.
- Zonta, C.; Cossu, S.; De Lucchi, O. Eur. J. Org. Chem. 2000, 1965-1971.
- Zonta, C.; De Lucchi, O.; Linden, A.; Lutz, M. Molecules 2010, 15, 226-232.
- Zonta, C.; Fabris, F.; De Lucchi, O. Org. Lett. 2005, 7, 1003-1006.
- Adam, W.; Balci, M.; Cakmak, O.; Peters, K.; Saha-M¨oller, C. R.; Schulz, M. Tetrahedron 1994, 50, 9009-9012.
- Adam, W.; Ahrweiler, M.; Balci, M.; Cakmak, O.; Saha-M¨oller, C. R. Tetrahedron Lett. 1995, 36, 1429-1430.
- Altundas, R.; Balci, M. Tetrahedron 1993, 49, 6521-6526.
- Laird, D. W.; Gilbert, J. C. J. Am. Chem. Soc. 2001, 123, 6704-6705.
- Tumer, F.; Taskesenligil, Y.; Balci, M. J. Org. Chem. 2001, 66, 3806-3810.
- De La Mare, P. B. D.; Bolton, R. In Electrophilic Additions to Unsaturated Systems, 2nd ed., Elsevier, New York, Lobanova, T. P.; Berus, E. I.; Barkhash, V. A. Zh. Obshch. Khim. 1969, 39, 2332 (Chemical Abstract Number: :43270).
- Dastan, A.; Balci, M. Tetrahedron 2005, 61, 5481-5488.
- Gultekin, D. D.; Taskesenligil, Y.; Dastan, A.; Balci, M. Tetrahedron 2008, 64, 4377-4383.
- Sengul, M. E.; Gultekin, D. D.; Essiz, S.; Dastan, A. Turk. J. Chem. 2009, 33, 79-86.
- Sengul, M. E.; Gultekin, D. D.; Essiz, S.; Sahin, E.; Dastan, A. Tetrahedron 2009, 65, 4859-4865.
- Taskesenlioglu, S.; Dastan, A.; Dalkilic, E.; Guney, M.; Abbasoglu, R. New J. Chem. 2010, 34, 141-150.
- Smith, W. B.; Saint, C.; Johnson, L. R. J. Org. Chem. 1984, 49, 3771-3774.
- Povolotskaya, N. N.; Limasova, T. I.; Berus, E. I.; Exner, O.; Barkhash, V. A. J. Org. Chem. USSR (Engl. Transl.) , 6, 1615.
- Hill, R. K.; Pendalwar, S. L.; Kielbasinski, K.; Baevsky, M. F.; Nugara, P. N. Synth. Commun. 1990, 20, 1877.
- Dastan, A. Tetrahedron 2001, 57, 8725-8732.
- Winstein, S. J. Am. Chem. Soc. 1961, 83, 1516-1517.
- Rigaku/MSC, Inc., 9009 New Trails Drive, The Woodlands, TX 77381, USA.
- Sheldrick, G. M. SHELXS97 and SHELXL97, University of G¨ottingen, Germany, 1997.