Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Halogenated Cleavage of Epoxides into Halohydrins in the Presence of a Series of Diamine Podands as Catalyst with Elemental Idoine and Bromine

  • Published : 2002.11.20
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Abstract

The ring opening of epoxides with elemental iodine and bromine in the presence of three diamine podands 7-9 as new catalysts affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under neutral and mild conditions in various aprotic solvents even when sensitive functional groups are presented.

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References

  1. Bonini, C.; Righi, G. Synthesis 1994, 225.
  2. Shimizu, M.; Yoshida, A.; Fujisawa, T. Synlett 1992, 204.
  3. Iranpoor, N.; Mohammadpour Baltork, I. Synth. Commun. 1990, 20, 2798.
  4. Smith, J. G. Synthesis 1984, 629.
  5. Kricheldorf, H. R.; Morber, G.; Regel, W. Synthesis 1981, 383.
  6. Andrews, G. C.; Grawford, T. C.; Contilio, L. G. Tetrahedron Lett. 1981, 22, 3803. https://doi.org/10.1016/S0040-4039(01)91312-7
  7. Detty, M. R.; Seidler, M. D. Tetrahedron Lett. 1982, 23, 2543. https://doi.org/10.1016/S0040-4039(00)87391-8
  8. Palumbo, G.; Ferreri, C.; Caputo, R. Tetrahedron Lett. 1983, 24, 1307 https://doi.org/10.1016/S0040-4039(00)81642-1
  9. Palumbo, G.; Ferreri, C.; Caputo, R. Synthesis 1986, 499.
  10. Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, C. J. Org. Chem. 1987, 52, 1680. https://doi.org/10.1021/jo00385a007
  11. Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246. https://doi.org/10.1021/ja00226a050
  12. Bell, T. W.; Ciaccio, J. A. Tetrahedron Lett. 1986, 27, 827. https://doi.org/10.1016/S0040-4039(00)84111-8
  13. Bovicelli, P.; Mincione, E.; Orttagi, G. Tetrahedron Lett. 1991, 32, 3719. https://doi.org/10.1016/S0040-4039(00)79777-2
  14. Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248.
  15. Guo, Z. X.; Haines, A. H.; Taylor, R. J. K. Synlett 1993, 607.
  16. Bajwa, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021. https://doi.org/10.1016/0040-4039(91)80676-W
  17. Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845. https://doi.org/10.1016/0040-4039(96)00159-1
  18. Konaklieva, M. I.; Dahi, M. L.; Turos, E. Tetrahedron Lett. 1992, 33, 7093 https://doi.org/10.1016/S0040-4039(00)60844-4
  19. Vogtle, F.; Weber, E. Angew. Chem. Int. Ed. Engl. 1979, 18, 753. https://doi.org/10.1002/anie.197907531
  20. Sharghi, H.; Massah, A. R.; Eshghi, H.; Niknam, K. J. Org. Chem. 1998, 63, 1455. https://doi.org/10.1021/jo971453y
  21. Sharghi, H.; Niknam, K.; Pooyan, M. Tetrahedron 2001, 57, 6057. https://doi.org/10.1016/S0040-4020(01)00443-4
  22. Gangali, M. R.; Eshghi, H.; Sharghi, H.; Shamsipur, M. J. Electroanal. Chem. 1996, 405, 177. https://doi.org/10.1016/0022-0728(95)04413-2
  23. Sharghi, H.; Massah, A. R.; Abedi, M. Talanta 1999, 49, 531. https://doi.org/10.1016/S0039-9140(99)00011-9
  24. Dawe, R. D.; Molinski, T. F.; Turner, J. V. Tetrahedron Lett. 1984, 25, 2061. https://doi.org/10.1016/S0040-4039(01)90113-3
  25. Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. Tetrahedron 1992, 48, 3805. https://doi.org/10.1016/S0040-4020(01)92271-9
  26. Dela Mare, P. B. D.; Bolton, R. Elctrophilic Addition to Unsaturated Systems; Elsevier Scientefic: Amsterdam, 1996; p. 132.
  27. Eisch, J. J.; Liu, Z. R.; Ma, X.; Zheng, G. X. J. Org. Chem. 1992, 57, 5140. https://doi.org/10.1021/jo00045a026
  28. Semnani, A.; Shamsipur, M. J. Chem. Soc. Dalton Trans. 1996, 2215.
  29. Hopkins, H. P.; Jahagirdar, D. V.; Windler, F. J. Phys. Chem. 1978, 82, 1254. https://doi.org/10.1021/j100500a012
  30. Nour, E. M.; Shahad, L. M. A. Spectrochim. Acta, Part A 1988, 44a, 1277.
  31. Nour, E. M. Spectrochim. Acta, part A 1991, 47a, 473.
  32. Lang, R. P. J. Phys. Chem. 1974, 78, 1657. https://doi.org/10.1021/j100609a012
  33. Andrews, L. J.; Prochaska, E. S.; Loewenschuss, A. Inorg. Chem. 1980, 19, 463. https://doi.org/10.1021/ic50204a036
  34. Mizuno, M.; Tanaka, J.; Harada, I. J. Phys. Chem. 1981, 85, 1789. https://doi.org/10.1021/j150613a006
  35. Serguchev, Y. A.; Petrenko, T. I. Teor. Eksp. Khim. 1977, 13, 705.
  36. Andrews, L. J.; Keefer, R. M. J. Org. Chem. 1987, 52, 2690. https://doi.org/10.1021/jo00389a011
  37. Mizuno, M.; Tanaka, J.; Harada, I. J. Phys. Chem. 1981, 85, 1789. https://doi.org/10.1021/j150613a006
  38. Dutasta, J.; Declercq, J.; Calderon, C. J. Am. Chem. Soc. 1989, 111, 7136. https://doi.org/10.1021/ja00200a036
  39. Iranpoor, N.; Kazemi, F.; Salehi, P. Synth. Commun. 1997, 27, 1247. https://doi.org/10.1080/00397919708003362
  40. Masuda, H.; Takase, K.; Nishio, M.; Hasegavw, A.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 5550. https://doi.org/10.1021/jo00098a012
  41. Guss, C. O.; Rosenthal, R. J. Am. Chem. Soc. 1955, 77, 2549.

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