Bulletin of the Korean Chemical Society

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Polyethylene Glycol: A Cheap and Efficient Medium for the Thiocyanation of Alkyl Halides

  • Published : 2008.12.20
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Abstract

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References

  1. Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64. https://doi.org/10.1039/b413546f
  2. Doble, M.; Kruthiventi, A. K. Green Chemistry & Engineering; Academic Press is an imprint of Elsevier: 2006; p 93.
  3. Prajapati, D.; Gohain, M. Tetrahedron 2004, 60(4), 815. https://doi.org/10.1016/j.tet.2003.10.075
  4. Chang, S. U.; Cho, J. H.; Lee, J. C. Bull. Korean Chem. Soc. 2008, 29, 27. https://doi.org/10.5012/bkcs.2008.29.1.027
  5. Tanaka, K. Solvent-free Organic Synthesis; Wiley-VCH: Weinheim, 2003.
  6. Chandrasekhar, S.; Narsihmulu, Ch.; Chandrashekar, G.; Shyamsunder, T. Tetrahedron Lett. 2004, 45, 2421. https://doi.org/10.1016/j.tetlet.2004.01.097
  7. Basaif, S. A.; Sobahi, T. R.; Khalil, A. K.; Hassan, M. A. Bull. Korean Chem. Soc. 2005, 26, 1677. https://doi.org/10.5012/bkcs.2005.26.11.1677
  8. Xu, B. L.; Chen, J. P.; Qiao, R. Z.; Fu, D. C. Chin. Chem. Lett. 2008, 19(5), 537.
  9. Santaniello, E.; Manzocchi, A.; Sozzani, P. Tetrahedron Lett. 1979, 47, 4581.
  10. Mehta, R. G.; Liu, J.; Constantinou, A.; Thomas, C. F.; Hawthorne, M.; You, M.; Gerhaeuser, C.; Pezzuto, J. M.; Moon, R. C.; Moriarty, R. M. Carcinogenesis 1995, 16, 399. https://doi.org/10.1093/carcin/16.2.399
  11. Metzer, J. B. In Comprehensive Heterocyclic Chemistry; Katritzky, A., Ed.; Pergamon: Oxford, 1984; Vol. 6, p 235.
  12. Buchel, K. H. Chemie der Pflanzen Schutz-Und Schadlingsbe Kampfungsmittle; Springer: Berlin Heidelberg, New York, 1970; p 457.
  13. Gerson, C.; Sabater, J.; Scuri, M.; Torbati, A.; Coffey, R.; Abraham, J. W.; Lauredo, I.; Forteza, R.; Wanner, A.; Salathe, M.; Abraham, W. M.; Conner, G. E. Am. J. Respir. Cell Mol. Biol. 2000, 22, 665. https://doi.org/10.1165/ajrcmb.22.6.3980
  14. Akio, M.; Masaaki, K. U. S. Patent 5,155,108; Chem. Abstr. 1991, 114, 102028e.
  15. Gorl, U.; Wolff, S. DE 4,100,217, 1992; Chem. Abstr. 1992, 117, 152581n.
  16. Batanero, B.; Braba, F.; Martina, A. J. Org. Chem. 2002, 67, 2369 https://doi.org/10.1021/jo016065h
  17. Vikharev, Y.; Shklyaev, Y.; Anikina, L.; Kolla, V.; Tolstikova, A. Pharm. Chem. J. 2005, 39, 405 https://doi.org/10.1007/s11094-005-0168-y
  18. Dittmer, D. C. Comprehensive Heterocyclic Chemistry; Katritzky, A., Ed.; Pergamon: Oxford, 1984; Vol. 7, p 178.
  19. Prakash, O.; Saini, N. Synth. Commun. 1993, 23, 1455. https://doi.org/10.1080/00397919308011236
  20. Brimeyer, M. O.; Mehrota, A.; Quici, S.; Nigam, A.; Regen, S. L. J. Org. Chem. 1980, 45, 4254. https://doi.org/10.1021/jo01309a047
  21. Kiasat, A. R.; Mehrjardi, M. F. Catal. Commun. 2008, 9, 1497 https://doi.org/10.1016/j.catcom.2007.12.019
  22. Kiasat, A. R.; Zayadi, M.; Mehrjardi, M. F. Chin. Chem. Lett. 2008, 19, 665 https://doi.org/10.1016/j.cclet.2008.04.004
  23. Das, B.; Reddy, V. S.; Krishnaiah, M. Tetrahedron Lett. 2006, 47, 8471. https://doi.org/10.1016/j.tetlet.2006.09.153
  24. Bacon, R. G. R.; Guy, R. G. J. Chem. Soc. 1961, 2447. https://doi.org/10.1039/jr9610002447
  25. Iranpoor, N.; Firouzabadi, H.; Nowrouzi, N. Tetrahedron 2006, 62, 5498. https://doi.org/10.1016/j.tet.2006.03.030

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