Bulletin of the Korean Chemical Society

  • 제32권2호
  • /
  • Pages.472-476
  • /
  • 2011
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

The Use of Sodium Chlorate/Hydrochloric Acid Mixtures as a Novel and Selective Chlorination Agent

  • 투고 : 2010.09.20
  • 심사 : 2010.11.29
  • 발행 : 2011.02.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the $\alpha$-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.

키워드

참고문헌

  1. de la Mare, P. B. D. Electrophilic Halogenation; Cambridge University Press: Cambridge, 1976.
  2. March, J. Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 4th ed.; John Wiley & Sons: New York, 1992; pp 531-534.
  3. Pearson, D. E.; Buehler, C. A. Synthesis 1971, 455.
  4. Taylar, R. Electrophilic Aromatic Substitution; John Wiley & Sons: Chichester, 1990;Ch. 9.
  5. De Kimpe, N.; De Bucyk, L.; Verhe, R.; Wychuyse, F.; Schamp, N. Syn. Comm. 1979, 9, 575. https://doi.org/10.1080/00397917908066703
  6. Jaeger, D. A.; Clennan, M. W.; Leyden,D. E.; Murthy, R. S. S. Tetrahedron Lett. 1987, 28, 4805. https://doi.org/10.1016/S0040-4039(00)96630-9
  7. Watson, W. D. J. Org. Chem. 1974, 39, 1160. https://doi.org/10.1021/jo00922a034
  8. Watson, W. D. J. Org. Chem. 1985, 50, 2145. https://doi.org/10.1021/jo00212a029
  9. Rutherford, K. G.; Stevens, C. L. J. Am. Chem. Soc. 1955, 77, 3278. https://doi.org/10.1021/ja01617a037
  10. Sisti, A. J.; Vitale, A. C. J. Org. Chem. 1972, 37, 4090. https://doi.org/10.1021/jo00798a025
  11. Cordell,G. A. J. Org. Chem. 1975, 40, 3161. https://doi.org/10.1021/jo00910a001
  12. Masilamani, D.; Rogic, M.M. J. Org. Chem. 1981, 46, 4486. https://doi.org/10.1021/jo00335a033
  13. Goldberg, Y.; Alper, H. J. Org. Chem. 1993, 58, 3072. https://doi.org/10.1021/jo00063a028
  14. Harpp,D. N.; Bao, L. Q.; Black, C. J.; Gleason, J. G.; Smith, R. A. J. Org. Chem. 1975, 40, 3420. https://doi.org/10.1021/jo00911a026
  15. Vaz, A. D. N.; Schoellmann, G. J. Org. Chem. 1984, 49, 1286. https://doi.org/10.1021/jo00181a033
  16. Hambly, G. F.; Chan, T. H. Tetrahedron Lett. 1986, 27, 2563. https://doi.org/10.1016/S0040-4039(00)84585-2
  17. Antelo, J. M.; Crugeir, F. A. J.; Parajo, C. M. J. Phys. Org. Chem. 1997, 10, 631. https://doi.org/10.1002/(SICI)1099-1395(199708)10:8<631::AID-POC924>3.0.CO;2-W
  18. Crocker, H. P.; Walser, R. J. Chem. Soc. C 1970, 1982.
  19. Ito,Y.; Nakatsuka, M.; Saegusa, T. J. Org. Chem. 1980, 45, 2022. https://doi.org/10.1021/jo01298a062
  20. Kosower, E. M.; Cole, W. J.; Wu, G. -S.; Cardy, D. E.; Meisters,G. J. Org. Chem. 1963, 28, 630. https://doi.org/10.1021/jo01038a007
  21. Bansal, S. R.; Nonhebel, D. C.;Mancilla, J. M. Tetrahedron 1973, 29, 993. https://doi.org/10.1016/0040-4020(73)80051-1
  22. Grossert, J. S.; Chip, G. K. Tetrahedron Lett. 1970, 11, 2611. https://doi.org/10.1016/S0040-4039(01)98293-0
  23. Wender, P. A.; Holt, D. A. J. Am. Chem. Soc. 1985, 107, 7771. https://doi.org/10.1021/ja00311a096
  24. Brummond, K. M.; Gesenberg, K. D. Tetrahedron Lett. 1999, 40,2231. https://doi.org/10.1016/S0040-4039(99)00213-0
  25. Roy, S. C.; Rana, K. K.; Guin, C.; Banerjee, B. ARKIVOC 2003,4, 34.
  26. Kurosawa, K.; Yamaguchi, K. Bull. Chem. Soc. Jpn. 1981, 54,1757. https://doi.org/10.1246/bcsj.54.1757
  27. Mukhopadhyay, S.; Mukhopadhyaya, J. K.; Ponde, D. E.;Cohen, S.; Kurkalli, B. G. S. Org. Process Res. Dev. 2000, 4, 509. https://doi.org/10.1021/op0000273
  28. Majetich, G.; Hicks, R.; Reister, S. J. Org. Chem. 1997, 62, 4321. https://doi.org/10.1021/jo970135w
  29. Kim, E-H.; Koo, B-S.; Song, C-E.; Lee, K-J. Syn. Commun.2001, 31, 3627. https://doi.org/10.1081/SCC-100107011
  30. Ben-Daniel, R.; de Visser, S. P.; Shaik, S.; Neumann,R. J. Am. Chem. Soc. 2003, 125, 12116. https://doi.org/10.1021/ja0364524
  31. Serguchev, Y. A.; Chernobaev, I. I. Theor. Exp. Chem. 2010, 46,102. https://doi.org/10.1007/s11237-010-9125-2
  32. Choi, H. Y.; Lee, B. S.; Chi, D. Y.; Kim, D. J. Heterocycles 1998,48, 2647. https://doi.org/10.3987/COM-98-8316

피인용 문헌

  1. ChemInform Abstract: The Use of Sodium Chlorate/Hydrochloric Acid Mixtures as a Novel and Selective Chlorination Agent. vol.42, pp.26, 2011, https://doi.org/10.1002/chin.201126034
  2. Decarbonylative Halogenation by a Vanadium Complex vol.52, pp.6, 2013, https://doi.org/10.1021/ic302611a
  3. 2,2,6,6-Tetramethylpiperidine-Catalyzed, Ortho-selective Chlorination of Phenols by Sulfuryl Chloride vol.79, pp.2, 2014, https://doi.org/10.1021/jo402424h
  4. and KCl under catalyst-free conditions vol.39, pp.5, 2015, https://doi.org/10.1039/C5NJ00118H
  5. In Situ Formed IIII‐Based Reagent for the Electrophilic ortho‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl3 System vol.2018, pp.4, 2011, https://doi.org/10.1002/ejoc.201701399
  6. Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids vol.26, pp.46, 2011, https://doi.org/10.1002/chem.202000902