Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant

Synthesis

Volumn , Issue 3, 2004, Pages 441-445

  Lulinski, Piotr ^a   Kryska, Anna ^a   Sosnowski, Maciej ^a   Skulski, Lech ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Arenes; Halogenation; Iodine; Iodoarenes; Peroxides

Indexed keywords

HYDROGEN BONDS; IODINE; ORGANIC COMPOUNDS; OXIDATION;

IODINATION;

HYDROGEN PEROXIDE;

HYDROGEN PEROXIDE; OXIDIZING AGENT; POLYCYCLIC AROMATIC HYDROCARBON; UREA DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFERENCE PAPER; HYDROGEN BOND; IODINATION; LABORATORY TEST; MOLECULAR STABILITY; OXIDATION; REACTION ANALYSIS; SOLID STATE;

EID: 1442286425     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815955     Document Type: Conference Paper

References (37)

1. These results were presented at the International Symposium on Frontiers in Molecular Science 2002, Qingdao, China, July 14-18, 2002.
2. Reviews on aromatic iodination: (a) Roedig, A. In Houben-Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4; Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517-678. (b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem. Rev. 1984, 53, 343. (c) Merkushev, E. B. Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of Halides, Pseudo-Halides, and Azides, Suppl. D1; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995, 535-620. (e) Steel, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Part 1, Vol. 3; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
3. Reviews on aromatic iodination: (a) Roedig, A. In Houben-Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4; Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517-678. (b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem. Rev. 1984, 53, 343. (c) Merkushev, E. B. Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of Halides, Pseudo-Halides, and Azides, Suppl. D1; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995, 535-620. (e) Steel, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Part 1, Vol. 3; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
4. Reviews on aromatic iodination: (a) Roedig, A. In Houben-Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4; Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517-678. (b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem. Rev. 1984, 53, 343. (c) Merkushev, E. B. Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of Halides, Pseudo-Halides, and Azides, Suppl. D1; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995, 535-620. (e) Steel, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Part 1, Vol. 3; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
5. Reviews on aromatic iodination: (a) Roedig, A. In Houben-Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4; Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517-678. (b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem. Rev. 1984, 53, 343. (c) Merkushev, E. B. Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of Halides, Pseudo-Halides, and Azides, Suppl. D1; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995, 535-620. (e) Steel, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Part 1, Vol. 3; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
6. Reviews on aromatic iodination: (a) Roedig, A. In Houben-Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4; Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517-678. (b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem. Rev. 1984, 53, 343. (c) Merkushev, E. B. Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of Halides, Pseudo-Halides, and Azides, Suppl. D1; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995, 535-620. (e) Steel, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Part 1, Vol. 3; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
7. Reviews on aromatic iodination: (a) Roedig, A. In Houben-Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4; Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517-678. (b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem. Rev. 1984, 53, 343. (c) Merkushev, E. B. Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of Halides, Pseudo-Halides, and Azides, Suppl. D1; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995, 535-620. (e) Steel, P. G. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Part 1, Vol. 3; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1996, 178-224.
8. For the latest reviews on organic hypervalent iodine compounds: (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: Weinheim, 1992. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (e) Hypervalent Iodine Chemistry, Vol. 224; Wirth, T., Ed.; Topics in Current Chemistry, Springer: Berlin, 2003. (f) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
9. For the latest reviews on organic hypervalent iodine compounds: (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: Weinheim, 1992. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (e) Hypervalent Iodine Chemistry, Vol. 224; Wirth, T., Ed.; Topics in Current Chemistry, Springer: Berlin, 2003. (f) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
10. For the latest reviews on organic hypervalent iodine compounds: (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: Weinheim, 1992. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (e) Hypervalent Iodine Chemistry, Vol. 224; Wirth, T., Ed.; Topics in Current Chemistry, Springer: Berlin, 2003. (f) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
11. For the latest reviews on organic hypervalent iodine compounds: (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: Weinheim, 1992. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (e) Hypervalent Iodine Chemistry, Vol. 224; Wirth, T., Ed.; Topics in Current Chemistry, Springer: Berlin, 2003. (f) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
12. For the latest reviews on organic hypervalent iodine compounds: (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: Weinheim, 1992. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (e) Hypervalent Iodine Chemistry, Vol. 224; Wirth, T., Ed.; Topics in Current Chemistry, Springer: Berlin, 2003. (f) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
13. For the latest reviews on organic hypervalent iodine compounds: (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: Weinheim, 1992. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (e) Hypervalent Iodine Chemistry, Vol. 224; Wirth, T., Ed.; Topics in Current Chemistry, Springer: Berlin, 2003. (f) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
14. (a) Skulski, L. Molecules 2000, 5, 1331; http:// www.mdpi.org/molecules/ papers/51201331.pdf.
15. 2 are discussed and referred to the literature: Kasumov, T. M.; Koz'min, A. S.; Zefirov, N. S. Usp. Khim. 1997, 66, 939; Russ. Chem. Rev. 1997, 66, 843.
16. 2 are discussed and referred to the literature: Kasumov, T. M.; Koz'min, A. S.; Zefirov, N. S. Usp. Khim. 1997, 66, 939; Russ. Chem. Rev. 1997, 66, 843.
17. Skulski, L. Molecules 2003, 8, 45; http://www.mdpi.org/ molecules/papers/80100045.pdf.
18. Krassowska-Swiebocka, B.; Lulinski, P.; Skulski, L. Synthesis 1995, 926.
19. Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 1997, 70, 1665.
20. Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 1999, 72, 115.
21. Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 2000, 73, 951.
22. (a) Kryska, A.; Skulski, L. J. Chem. Res., Synop. 1999, 591.
23. (b) Kryska, A.; Skulski, L. J. Chem. Res., Miniprint 1999, 2501.
24. Lu, C-S.; Hughes, E. W.; Giguere, P. A. J. Am. Chem. Soc. 1941, 63, 1507.
25. Tanatar, S. J. J. Russ. Phys. Chem. Soc. 1906, 40L, 376; Chem. Abstr. 1909, 3, 383.
26. Tanatar, S. J. J. Russ. Phys. Chem. Soc. 1906, 40L, 376; Chem. Abstr. 1909, 3, 383.
27. (a) Lancaster 2002-3 Forschungschemikalien; Lancaster: Mühlheim, 2002-2003, 1761; see also exemplary applications of UHP given therein.
28. (b) Aldrich Handbook of Fine Chemicals and Laboratory Equipment; Aldrich: Milwaukee, 2003-2004, 1898.
29. (c) The Merck Index, 12th ed.; Merck & Co., Inc.: Rahway, 1996, 10007.
30. Chen, J.-A.; Lin, C.-S.; Liu, L. K. J. Chin. Chem. Soc. (Taipei) 1996, 43, 95; see also refs. 9, 10 therein, Chem. Abstr. 1996, 124, 288874.
31. Chen, J.-A.; Lin, C.-S.; Liu, L. K. J. Chin. Chem. Soc. (Taipei) 1996, 43, 95; see also refs. 9, 10 therein, Chem. Abstr. 1996, 124, 288874.
32. Adimurthy, S.; Ramachandraiah, G.; Ghosh, P. K.; Bedekar, A. V. Tetrahedron Lett. 2003, 44, 5099.
33. Sosnowski, M.; Skulski, L. Molecules 2002, 7, 867; http:// www.mdpi.org/molecules/papers/71200867.pdf.
34. 4 pp 1334-1337.
35. Dictionary of Organic Compounds, 6th ed.; Chapman & Hall: London, 1996.
36. 4 mixtures to give N-acetylurea admixed with N,N′-diacetylurea. However, these side products are fully removable from the crude iodinated products during the workup and recrystallization.
37. 1H NMR solution spectra run in this work to support the structures of the purified iodinated products are presented and discussed in: Lulinski P.; Ph.D. Thesis (in Polish); Faculty of Pharmacy, Medical University of Warsaw: Poland, 2002;