Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Facile and Efficient Selective Mono-nitration of Phenols under Solvent-free Conditions

  • Beheshti, S. (School of Chemistry, University College of Science, University of Tehran) ;
  • Kianmehr, E. (School of Chemistry, University College of Science, University of Tehran) ;
  • Yahyaee, M. (School of Chemistry, University College of Science, University of Tehran) ;
  • Tabatabai, K. (School of Chemistry, University College of Science, University of Tehran)
  • 발행 : 2006.01.20
Download PDF
⟨ Previous Next ⟩

초록

키워드

참고문헌

  1. Olah, G. A.; Malhorta, R.; Narang, S. C. Nitration: Methods and Mechanism; VCH: New York, 1989
  2. Schofield, K. Aromatic Nitrations; Cambridge University Press: Cambridge, 1980
  3. Zolfigol, M. A.; Mirjalili, B. F.; Bamoniri, A.; Karimi Zarchi, M. A.; Zarei, A.; Khazdooz, L.; Noei, J. Bull. Korean Chem. Soc. 2004, 25, 1414 https://doi.org/10.5012/bkcs.2004.25.9.1414
  4. Lee, K. J.; Lee, S. H. J. Korean Chem. Soc. 2001, 45, 538
  5. Kwon, P. S.; Kim, J. K.; Kwon, T. W.; Kim, Y. H.; Chung, S. K. Bull. Korean Chem. Soc. 1997, 18, 1118
  6. Nam, K. C.; Kim, D. S. Bull. Korean Chem. Soc. 1994, 15, 284
  7. Peng, X.; Suzuki, H.; Lu, C. Tetrahedron Lett. 2001, 42, 4357 https://doi.org/10.1016/S0040-4039(01)00750-X
  8. Bak, R. R.; Smallridge, A. Tetrahedron Lett. 2001, 42, 6767 https://doi.org/10.1016/S0040-4039(01)01378-8
  9. Olah, G. A.; Kuhn, S. J. J. Am. Chem. Soc. 1962, 84, 3684 https://doi.org/10.1021/ja00878a018
  10. Iranpoor, N.; Firouzabadi, H.; Heydari, R. Synth. Commun. 1999, 29, 3295 https://doi.org/10.1080/00397919908085957
  11. Zolfigol, M. A.; Ghasemi, E.; Madrakian, E. Synlett 2003, 191
  12. Riego, J. M.; Sedin, Z.; Zaldivar, J. M.; Marziano, N. C.; Tortato, C. Tetrahedron Lett. 1996, 37, 513 https://doi.org/10.1016/0040-4039(95)02174-4
  13. Bahulayan, D.; Narayan, G.; Sreekumar, V.; Lalithambika, M. Synth. Commun. 2002, 32, 3565 https://doi.org/10.1081/SCC-120014967
  14. Cornelis, A.; Laszlo, P. Synthesis 1985, 909
  15. Samajdar, S.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 8017 https://doi.org/10.1016/S0040-4039(00)01397-6
  16. Tasneem, A. M. M.; Rajanna, K. C.; Saiparakash, P. K. Synth. Commun. 2001, 31, 1123 https://doi.org/10.1081/SCC-100103545
  17. Braddock, C. Green Chem. 2001, 3, 26 https://doi.org/10.1039/b008795p
  18. Geletii, Y. V.; Bailey, A. J.; Cowan, J. J.; Weinstock, I. A.; Hill, C. L. Can. J. Chem. 2001, 79, 792 https://doi.org/10.1139/cjc-79-5-6-792
  19. Zolfigol, M. A.; Ghaemi, E.; Madrakian, E. Molecules 2001, 6, 614 https://doi.org/10.3390/60700614
  20. Dove, M. F. A.; Manz, B.; Montgomery, J.; Pattenden, G.; Wood, S. A. J. Chem. Soc., Perkin Trans. 1 1998, 1589
  21. Zolfigol, M. A.; Bagherzadeh, M.; Madrakian, E.; Ghaemi, E.; Taqian-Nasab, A. J. Chem. Res. (S) 2001, 4, 140
  22. Suzuki, H.; Yonezawa, S.; Nonoyama, N.; Mori, T. J. Chem. Soc., Perkin Trans. 1 1996, 2385
  23. Kimura, M.; Kajita, K.; Naoyuki, O.; Morosawa, S. J. Org. Chem. 1990, 55, 4887 https://doi.org/10.1021/jo00303a024
  24. Laali, K. K.; Gettwert, V. J. J. Org. Chem. 2001, 66, 35 https://doi.org/10.1021/jo000523p
  25. Bose, A. K.; Ganguly, S. N.; Manhas, M. S.; Srirajan, V.; Bhattacharjee, A.; Rumthao, S.; Sharma, A. H. Tetrahedron Lett. 2004, 45, 1179 https://doi.org/10.1016/j.tetlet.2003.12.002
  26. Lehnig, M. Tetrahedron Lett. 1999, 40, 2299 https://doi.org/10.1016/S0040-4039(99)00277-4
  27. Nonoyama, N.; Chiba, K.; Hisatom, K.; Suzuki, H.; Shintani, F. Tetrahedron Lett. 1999, 40, 6923 https://doi.org/10.1016/S0040-4039(99)01443-4
  28. Rodrigues, J. A. R.; Filho, A. P. O.; Moran, P. J. S. Tetrahedron 1999, 55, 6733 https://doi.org/10.1016/S0040-4020(99)00320-8
  29. Iranpoor, N.; Firouzabadi, H.; Zolfigol, M. A. Bull. Chem. Soc. Jpn. 1998, 71, 905 https://doi.org/10.1246/bcsj.71.905
  30. Firouzabadi, H.; Iranpoor, N.; Zolfigol, M. A. Bull. Chem. Soc. Jpn. 1998, 71, 2169 https://doi.org/10.1246/bcsj.71.2169
  31. Firouzabadi, H.; Iranpoor, N.; Zolfigol, M. A. Synth. Commun. 1998, 28, 1179 https://doi.org/10.1080/00397919808005959
  32. Herrerías, C. I.; Zhang, T. Y.; Li, C. J. Tetrahedron Lett. 2006, 47, 13 https://doi.org/10.1016/j.tetlet.2005.10.123
  33. Jia, C. S.; Zhang, Z.; Tu, S. J.; Wang, G. W. Org. Biomol. Chem. 2006, 4, 104 https://doi.org/10.1039/b513721g
  34. Placzek, A. T.; Donelson, J. L.; Trivedi, R.; Gibbs, R. A.; De, S. K. Tetrahedron Lett. 2005, 46, 9029 https://doi.org/10.1016/j.tetlet.2005.10.106
  35. Petersson, A. E. V.; Gustafsson, L. M.; Nordblad, M.; Borjesson, P.; Mattiasson, B.; Adlercreutz, P. Green Chem. 2005, 7, 837 https://doi.org/10.1039/b510815b
  36. Bougrin, K.; Loupy, A.; Soufiaoui, M. J. Photochem. Photobiol. Rev. 2005, 6, 139 https://doi.org/10.1016/j.jphotochemrev.2005.07.001
  37. Shirini, F.; Zolfigol, M. A.; Mohammadpoor- Baltork, I.; Abedidni, M. Bull. Korean Chem. Soc. 2005, 26, 1833 https://doi.org/10.5012/bkcs.2005.26.11.1833
  38. Bandgar, B. P.; Patil, A. V. Tetrahedron Lett. 2005, 46, 7627 https://doi.org/10.1016/j.tetlet.2005.08.111
  39. Guillot, R.; Loupy, A.; Meddour, A.; Pellet, M.; Petit, A. Tetrahedron 2005, 61, 10129 https://doi.org/10.1016/j.tet.2005.07.040
  40. Lin, Q.; Zhang, Y. M.; Wei, T. B.; Wang, H. J. Chem. Res. (S) 2004, 298
  41. Kimmich, B. F. M.; Fagan, P. J.; Hauptman, E.; Marshall, W. J.; Bullock, R. M. Organometallics 2005, 24, 6220 https://doi.org/10.1021/om050564h
  42. Hajipour, A. R.; Bagheri, H. R.; Ruoho, A. E. Bull. Korean Chem. Soc. 2004, 25, 1238 https://doi.org/10.5012/bkcs.2004.25.8.1238
  43. Jeon, S. J.; Li, H. M.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 16416 https://doi.org/10.1021/ja052200m
  44. Besra, R. C.; Rudrawar, S.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 6213 https://doi.org/10.1016/j.tetlet.2005.07.059
  45. Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A. Green Chem. 2005, 7, 825 https://doi.org/10.1039/b511003c
  46. Taguchi, K.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2005, 46, 4539 https://doi.org/10.1016/j.tetlet.2005.05.013
  47. Shirini, F.; Zolfigol, M. A.; Mohammadi, K. Bull. Korean Chem. Soc. 2004, 25, 325 https://doi.org/10.5012/bkcs.2004.25.2.325
  48. Shirini, F.; Zolfigol, M. A.; Khaleghi, M. Bull. Korean Chem. Soc. 2003, 24, 1021 https://doi.org/10.5012/bkcs.2003.24.7.1021
  49. Iranpoor, N.; Firouzabadi, H.; Heydari, R. Synth. Commun. 1999, 29, 3295 https://doi.org/10.1080/00397919908085957
  50. Poirier, J.; Vottero, C. Tetrahedron 1989, 45, 1415 https://doi.org/10.1016/0040-4020(89)80139-5
  51. Corneils, A.; Laszlo, P. Synthesis 1985, 909
  52. Muathen, H. A. Molecules 2003, 8, 593 https://doi.org/10.3390/80700593
  53. Sathunuru, R.; Rao, U. N.; Biehl, E. ARKIVOK 2003, (xv), 124
  54. Dove, M. F. A.; Manz, B.; Montgomery, J.; Pattenden, G.; Wood, S. A. J. Chem. Soc. Perkin Trans. 1 1998, 1589

피인용 문헌

  1. Selective Nitration of Phenolic Compounds by Green Synthetic Approaches vol.44, pp.16, 2014, https://doi.org/10.1080/00397911.2014.896925
  2. Facile and Efficient Selective Mono-Nitration of Phenols under Solvent-Free Conditions. vol.37, pp.49, 2006, https://doi.org/10.1002/chin.200649038
  3. Highly Efficient Nitration of Phenolic Compounds using Some Nitrates and Oxalic Acid under Solvent-Free Conditions vol.35, pp.2, 2006, https://doi.org/10.3184/030823411x12935549795603