An efficient protocol for the synthesis of brominated norbornene, norbornadiene, and benzonorbornadiene

An efficient protocol for the synthesis of brominated norbornene, norbornadiene, and benzonorbornadiene

An efficient protocol for the synthesis of 2-bromonorbornene, 2-bromonorbornadiene, 2-bromoben- zonorbornadiene, 2,3-dibromonorbornene, 2,3-dibromonorbornadiene, and 2,3-dibromobenzonorbornadiene in good yields hasbeen developed. 1,2-Dibromotetrachloroethane is used as the brominating agent for these reactions. The results arediscussed in comparison with alternative methods in the literature.

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  • 1. Lennartson, A.; Roffey, A.; Moth-Poulsen, K. Tetrahedron Lett. 2015, 56, 1457-1465.
  • 2. Gray, V.; Lennartson, A.; Ratanalert, P.; Borjesson, K.; Moth-Poulsen, K. Chem. Commun. 2014, 50, 5330-5332.
  • 3. Tebikachew, B. E.; Li, H. B.; Pirrotta, A.; Borjesson, K.; Solomon, G. C.; Hihath, J.; Moth-Poulsen, K. J. Phys. Chem. 2017, 121, 7094-7100.
  • 4. Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165.
  • 5. Durr, R.; Cossu, S.; De Lucchi, O. Synth. Commun. 1997, 27, 1369-1372.
  • 6. Tam, W.; Cockburn, N. Synlett 2010, 1170-1189.
  • 7. Tranmer, G. K.; Tam, W. J. Org. Chem. 2001, 66, 5113-5123.
  • 8. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508-11509.
  • 9. Kocak, R.; Borsato, G.; De Lucchi, O.; Dastan, A. Helv. Chim. Acta 2014, 97, 537-545.
  • 10. Higashibayashi, S.; Reza, A. F. G. M.; Sakurai, H. J. Org. Chem. 2010, 75, 4626-4628.
  • 11. Cossu, S.; De Lucchi, O.; Paulon, A.; Peluso, P.; Zonta, C. Tetrahedron Lett. 2001, 42, 3515-3518.
  • 12. Cossu, S.; De Lucchi, O.; Lucchini, V.; Valle, G.; Balci, M.; Dastan, A.; Demirci, B. Tetrahedron Lett. 1997, 38, 5319-5322.
  • 13. Mayo, P.; Tam, W. Tetrahedron 2002, 58, 9513-9525.
  • 14. Mayo, P.; Tam, W. Tetrahedron 2002, 58, 9527-9540.
  • 15. Kenndoff, J.; Polborn, K.; Szeimies, G. J. Am. Chem. Soc. 1990, 112, 6117-6118.
  • 16. Peluso, P.; Greco, C.; De Lucchi, O.; Cossu, S. Eur. J. Org. Chem. 2002, 4024-4031.
  • 17. Tranmer, G. K.; Yip, C.; Handerson, S.; Jordan, R. W.; Tam, W. Can. J. Chem. 2000, 78, 527-535.
  • 18. Wang, Y.; Liu, J.; Huang, L.; Zhu, R.; Huang, X.; Moir, R.; Huang, J. Chem. Commun. 2017, 53, 4589-4592.
  • 19. Lennartson, A.; Quant, M.; Moth-Poulsen, K. Synlett 2015, 26, 1501-1504.
  • 20. Jung, S. H.; Hwang, G. S.; Lee, S. I.; Ryu, D. H. J. Org. Chem. 2012, 77, 2513-2518.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK