Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 4, 2000, Pages 951-956

  Luliński, Piotr ^a   Skulski, Lech ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; N,N DIMETHYLANILINE; PERIODATE SODIUM; POLYCYCLIC AROMATIC HYDROCARBON; SODIUM IODATE; SULFURIC ACID; TOLUENE;

ARTICLE; BROMINATION; CHEMICAL REACTION KINETICS; IODINATION; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0034015470     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.951     Document Type: Article

References (45)

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7. 3 iodinating species see: d) J. Arotsky, R. Butler, and A. C. Darby, J. Chem. Soc. C, 1970, 1480.
8. 3 iodinating species see: d) J. Arotsky, R. Butler, and A. C. Darby, J. Chem. Soc. C, 1970, 1480.
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10. The subsequent annual reviews on "Organic Halides," covering also aromatic iodides: a) P. L. Spargo, Contemp. Org. Synth., 1, 113 (1994). b) P. L. Spargo, Contemp. Org. Synth., 2, 85 (1995). c) S. P. Marsden, Contemp. Org. Synth., 3, 133 (1996). d) S. P. Marsden, Contemp. Org. Synth., 4, 118 (1997). e) S. D. R. Christie, J. Chem. Soc., Perkin Trans. 1, 1998, 1577. f) S. D. R. Christie, J. Chem. Soc., Perkin Trans, 1, 1999, 737.
11. The subsequent annual reviews on "Organic Halides," covering also aromatic iodides: a) P. L. Spargo, Contemp. Org. Synth., 1, 113 (1994). b) P. L. Spargo, Contemp. Org. Synth., 2, 85 (1995). c) S. P. Marsden, Contemp. Org. Synth., 3, 133 (1996). d) S. P. Marsden, Contemp. Org. Synth., 4, 118 (1997). e) S. D. R. Christie, J. Chem. Soc., Perkin Trans. 1, 1998, 1577. f) S. D. R. Christie, J. Chem. Soc., Perkin Trans, 1, 1999, 737.
12. The subsequent annual reviews on "Organic Halides," covering also aromatic iodides: a) P. L. Spargo, Contemp. Org. Synth., 1, 113 (1994). b) P. L. Spargo, Contemp. Org. Synth., 2, 85 (1995). c) S. P. Marsden, Contemp. Org. Synth., 3, 133 (1996). d) S. P. Marsden, Contemp. Org. Synth., 4, 118 (1997). e) S. D. R. Christie, J. Chem. Soc., Perkin Trans. 1, 1998, 1577. f) S. D. R. Christie, J. Chem. Soc., Perkin Trans, 1, 1999, 737.
13. The subsequent annual reviews on "Organic Halides," covering also aromatic iodides: a) P. L. Spargo, Contemp. Org. Synth., 1, 113 (1994). b) P. L. Spargo, Contemp. Org. Synth., 2, 85 (1995). c) S. P. Marsden, Contemp. Org. Synth., 3, 133 (1996). d) S. P. Marsden, Contemp. Org. Synth., 4, 118 (1997). e) S. D. R. Christie, J. Chem. Soc., Perkin Trans. 1, 1998, 1577. f) S. D. R. Christie, J. Chem. Soc., Perkin Trans, 1, 1999, 737.
14. The subsequent annual reviews on "Organic Halides," covering also aromatic iodides: a) P. L. Spargo, Contemp. Org. Synth., 1, 113 (1994). b) P. L. Spargo, Contemp. Org. Synth., 2, 85 (1995). c) S. P. Marsden, Contemp. Org. Synth., 3, 133 (1996). d) S. P. Marsden, Contemp. Org. Synth., 4, 118 (1997). e) S. D. R. Christie, J. Chem. Soc., Perkin Trans. 1, 1998, 1577. f) S. D. R. Christie, J. Chem. Soc., Perkin Trans, 1, 1999, 737.
15. The subsequent annual reviews on "Organic Halides," covering also aromatic iodides: a) P. L. Spargo, Contemp. Org. Synth., 1, 113 (1994). b) P. L. Spargo, Contemp. Org. Synth., 2, 85 (1995). c) S. P. Marsden, Contemp. Org. Synth., 3, 133 (1996). d) S. P. Marsden, Contemp. Org. Synth., 4, 118 (1997). e) S. D. R. Christie, J. Chem. Soc., Perkin Trans. 1, 1998, 1577. f) S. D. R. Christie, J. Chem. Soc., Perkin Trans, 1, 1999, 737.
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22. 6 reagent.
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28. 5 to activate diiodine without being consumed. Later, the extensive kinetic studies of an aromatic iodination reaction using benzene or acetanilide, iodine, diiodine pentaoxide and sulfuric acid in acetic acid have been carried out; see: L. C. Brazdil, J. L. Fitch, C. J. Cutler, D. M. Haynik, and E. R. Ace, J. Chem. Soc., Perkin Trans. 2, 1998, 933.
29. 5 to activate diiodine without being consumed. Later, the extensive kinetic studies of an aromatic iodination reaction using benzene or acetanilide, iodine, diiodine pentaoxide and sulfuric acid in acetic acid have been carried out; see: L. C. Brazdil, J. L. Fitch, C. J. Cutler, D. M. Haynik, and E. R. Ace, J. Chem. Soc., Perkin Trans. 2, 1998, 933.
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32. H. Suzuki, Org. Synth., 51, 94 (1971) or Coll. Vol. VI, p. 700.
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36. G. Ciustea and A. Panescu, Rev. Chim. (Bucharest), 20, 216 (1969); Chem. Abstr., 71, 123755 (1969). This short communication, with no experimental details and physico-chemical support. was never followed up either then or after 1969 by the more detailed experimental paper. The same is true in respect to Ref. 14
37. 4, 98%, 34.30 DM/100 g.
38. a) F. M. Beringer, M. Drexler, E. M. Gindler, and C. C. Lumpkin, J. Am. Chem. Soc., 75, 2705 (1953).
39. b) F. M. Beringer, R. A. Falk, M. Karniol, I. Lillien, G. Masullo, M. Mausner, and E. Sommer, J. Am. Chem. Soc., 81, 342 (1959).
40. 3-. This iodination method has never been published in a more detailed form.
41. 3-. This iodination method has never been published in a more detailed form.
42. 3 in acetic acid to give, besides 4-iodo-N,N-dimethylaniline, a mixture of three other products; for more details see: S. Ghosal, J. Indian Chem. Soc., 42, 799 (1965); see also Ref. 10 above, p. 242.
43. 4.
44. +" prepared on a base of toxic iodine chloride and silver sulfate, at 0-20 °C and within 15-150 min. Also, nearly all the former iodinating procedures suitable for deactivated aromatics are briefly reviewed therein - with excluding, however. Refs. 6 and 7.
45. +" prepared on a base of toxic iodine chloride and silver sulfate, at 0-20 °C and within 15-150 min. Also, nearly all the former iodinating procedures suitable for deactivated aromatics are briefly reviewed therein - with excluding, however. Refs. 6 and 7.