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DOI: 10.1039/A805063E (Paper) Reference Section for: J. Chem. Res. (S), 1999, 64-65

Oxidative Chlorination of Various Iodoarenes to (Dichloroiodo)arenes with Chromium(VI) Oxide as the Oxidant

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Pawet Kaźmierczak, Lech Skulski and Nicolas Obeid

Abstract

Chromium(VI) oxide dissolved in a mixture of acetic acid with concentrated hydrochloric acid converts, at or near room temperature, iodoarenes to (dichloroiodo)arenes, in a very simple and efficient procedure.

References

  1. A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, New York, Weinheim, Cambridge, 1992 Search PubMed .
  2. A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, London, 1997 Search PubMed .
  3. P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123 CrossRef CAS .
  4. A. Varvoglis, Tetrahedron, 1997, 53, 1179 CrossRef CAS .
  5. R. M. Moriarty and O. Prakash, Adv. Heterocycl. Chem., 1998, 69, 1 CAS .
  6. T. Kitamura and Y. Fujiwara, Org. Prep. Proced. Int., 1995, 3, 261 .
  7. C. Willgerodt, Die organischen Verbindungen mit mehrvertigem Jod, Enke, Stuttgart, 1914 Search PubMed .
  8. H. J. Lucas and E. R. Kennedy, Org. Synth., Coll. Vol. III, Wiley, New York, 1955, p. 482 Search PubMed .
  9. R. T. Taylor and T. A. Stevenson, Tetrahedron Lett., 1988, 29, 2033 CrossRef CAS  and references therein.
  10. A. Zanka, H. Takeuchi and A. Kubota, Org. Process Res. Dev., 1998, 2, 270 Search PubMed .
  11. A. Töhl, Ber. Dtsch. Chem. Ges., 1893, 26, 2949 Search PubMed .
  12. B. Ya. Karele and O. Ya. Neiland, Latv. PSR Zinat. Akad. Vestis, Kim. Ser., 1970, 587 Search PubMed ; Chem. Abstr. 1971, 74, 42033. They failed to chlorinate three iodonitrobenzenes, 4-iodobenzoic acid, and 2-iodoacetophenone; for ten appropriate iodobenzenes the crude yields for ArICl2 were 73–96% Search PubMed .
  13. D. I. Makhon'kov, A. V. Cheprakov and I. P. Beletskaya, Zh. Org. Khim., 1986, 22, 681 CAS ; Chem. Abstr., 1987, 106, 155951. Only iodobenzene was chlorinated there to give PhICl2(75%; 94% purity) Search PubMed .
  14. D. Koyunçu, A. McKillop and L. McLaren, J. Chem. Res. (S), 1990, 21 Search PubMed  They failed to chlorinate 2-iodonitrobenzene; for fifteen appropriate iodobenzenes the crude yields for ArICl2 were 60–98%.
  15. H. Fischli, Ber. Dtsch. Chem. Ges., 1878, 11, 1461 Search PubMed .
  16. A. Mannino and L. di Donato, Gazz. Chim. Ital., 1908, 38, II, 20 CAS .
  17. T. H. Durrans, J. Chem. Soc., 1923, 123, 1424 RSC .
  18. F. M. Beringer and E. M. Gindler, Iodine Abstr. Rev., 1956, 3, 1 Search PubMed .
  19. C. K. Ingold, E. W. Smith and C. C. N. Vass, J. Chem. Soc., 1927, 1245 RSC .
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