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Journals / Turkish Journal of Chemistry / 2011 / Cilt: 35 - Sayı: 4

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

Selçuk EŞSİZ
Mehmet Emin ŞENGÜL*
Ertan ŞAHİN
Arif DAŞTAN
Pages
587–598
Publication Date
2011-04-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Herein, we report the results of the synthesis, and the X-ray crystal structures and the possible mechanism of processes are discussed.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The bromination reaction of dihydrobenzobarrelene under different conditions was studied.
📊
Key Findings & Data:The bromination reaction of the alkene with 1,2- dibromotetrachloroethane (DBTCE) gave a non-rearrangement product as the sole product.
💡
Conclusion & Impact:Herein, we report the results of the synthesis, and the X-ray crystal structures and the possible mechanism of processes are discussed.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Bromination · benzobarrelene · Wagner-Meerwein rearrangement

Abstract

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.

Özet

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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Cite This Article

EŞSİZ, S., ŞENGÜL*, M. E., ŞAHİN, E., DAŞTAN, A. (2011). Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel. Turkish Journal of Chemistry, Cilt: 35 - Sayı: 4, 587–598. https://ajindex.com/articles/185179

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References (24)

  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, 563. Cossu, S.; Cimenti, C.; Peluso, P.; Paulon, A.; De Lucchi, O. Angew. Chem. Int. Edit. 2001, 40, 4086-4089.
  5. Dalkilic, E.; Guney, M.; Dastan, A.; Saracoglu, N.; De Lucchi, O.; Fabris, F. Tetrahedron Lett. 2009, 50, 1989-1991.
  6. Dastan, A.; Fabris, F.; De Lucchi, O.; Guney, M.; Balci, M. Helv. Chim. Acta 2003, 86, 3411-3416.
  7. De Lucchi, O.; Dastan, A.; Altundas, A.; Fabris, F.; Balci, M. Helv. Chim. Acta 2004, 87, 2364-2367.
  8. Durr, R.; Cossu, S.; Lucchini, V.; De Lucchi, O. Angew. Chem. Int. Edit. 1997, 36, 2805-2807.
  9. Fabris, F.; Bellotto, L.; De Lucchi, O. Tetrahedron Lett. 2003, 44, 1211-1213.
  10. Fabris, F.; Pellizzaro, L.; Zonta, C.; De Lucchi, O. Eur. J. Org. Chem. 2007, 283-291.
  11. Padovan, P.; Tartaggia, S.; Lorenzon, S.; Rosso, E.; Zonta, C.; De Lucchi, O.; Fabris, F. Tetrahedron Lett. 2009,, 1973-1976.
  12. Zonta, C.; Cossu, S.; De Lucchi, O. Eur. J. Org. Chem. 2000, 1965-1971.
  13. Zonta, C.; De Lucchi, O.; Linden, A.; Lutz, M. Molecules 2010, 15, 226-232.
  14. Zonta, C.; Fabris, F.; De Lucchi, O. Org. Lett. 2005, 7, 1003-1006.
  15. Adam, W.; Balci, M.; Cakmak, O.; Peters, K.; Saha-M¨oller, C. R.; Schulz, M. Tetrahedron 1994, 50, 9009-9012.
  16. Adam, W.; Ahrweiler, M.; Balci, M.; Cakmak, O.; Saha-M¨oller, C. R. Tetrahedron Lett. 1995, 36, 1429-1430.
  17. Altundas, R.; Balci, M. Tetrahedron 1993, 49, 6521-6526.
  18. Laird, D. W.; Gilbert, J. C. J. Am. Chem. Soc. 2001, 123, 6704-6705.
  19. Tumer, F.; Taskesenligil, Y.; Balci, M. J. Org. Chem. 2001, 66, 3806-3810.
  20. 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.
  21. Gultekin, D. D.; Taskesenligil, Y.; Dastan, A.; Balci, M. Tetrahedron 2008, 64, 4377-4383.
  22. Sengul, M. E.; Gultekin, D. D.; Essiz, S.; Dastan, A. Turk. J. Chem. 2009, 33, 79-86.
  23. Sengul, M. E.; Gultekin, D. D.; Essiz, S.; Sahin, E.; Dastan, A. Tetrahedron 2009, 65, 4859-4865.
  24. Taskesenlioglu, S.; Dastan, A.; Dalkilic, E.; Guney, M.; Abbasoglu, R. New