Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid

Tetrahedron

Volumn 60, Issue 41, 2004, Pages 9113-9119

  Kraszkiewicz, Lukasz ^a   Sosnowski, MacIej ^a   Skulski, Lech ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Deactivated arenes; Direct oxidative iodination; Iodine; Iodoarenes; Oxidation

Indexed keywords

BENZOIC ACID; CHROMIUM DERIVATIVE; IODINE DERIVATIVE; MANGANESE DIOXIDE; NITROBENZENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFURIC ACID;

ARTICLE; CRYSTALLIZATION; IODINATION; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; X RAY ANALYSIS;

EID: 4444304988     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.095     Document Type: Article

References (33)

1. A. Roedig Houben-Weyl, Methoden der organichen Chemie Vol. V/4 1960 517 678
2. E.B. Merkushev Synthesis 1988 923 937
3. A. Varvoglis The Organic Chemistry of Polycoordinated Iodine 1992 VCH Weinheim
4. P.J. Stang, and V.V. Zhdankin Chem. Rev. 96 1996 1123 1178
5. A. Varvoglis Hypervalent Iodine in Organic Synthesis 1997 Academic Press San Diego
6. V.V. Zhdankin, and P.J. Stang Chem. Rev. 102 2002 2523 2584
7. P.J. Stang J. Org. Chem. 68 2003 2997 3008
8. (f) Hypervalent Iodine Chemistry Topics in Current Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
9. L. Skulski Molecules 5 2000 1331 1371 http://www.mdpi.org/molecules
10. L. Skulski Molecules 8 2003 45 52 http://www.mdpi.org/molecules
11. I. Masson J. Chem. Soc. 1938 1708 1712
12. I.R.L. Baker, and W.A. Waters J. Chem. Soc. 1952 150 153
13. J. Arotsky, R. Butler, and A.C. Darby J. Chem. Soc. (C) 1970 1480 1485
14. G.A. Olah, Q. Wang, G. Sandford, and G.K.S. Prakash J. Org. Chem. 58 1993 3194 3195
15. Y. Kobayashi, I. Kumadaki, and T. Yoshida J. Chem. Res. (S) 1997 215
16. R.D. Chambers, C.J. Skinner, M.J. Atherton, and J.S. Moilliet J. Chem. Soc., Perkin Trans. 1 1995 1659 1664
17. V.K. Chaikovski, T.S. Kharlova, V.D. Filimonov, and T.A. Saryucheva Synthesis 1999 748 750
18. V.K. Chaikovski, T.S. Kharlova, and V.D. Filimonov Russ. Chem. Bull. 48 1999 1291 1294
19. V.K. Chaikovski, V.D. Filimonov, T.S. Kharlova, T.N. Chernova, and E.S. Sharapova Russ. J. Org. Chem. 36 2000 666 670
20. V.K. Chaikovski, V.D. Filimonov, Yu.A. Yagovkin, and T.S. Kharlova Tetrahedron Lett. 41 2000 9101 9104
21. V.K. Chaikovski, V.I. Skorokhodov, and V.D. Filimonov Russ. J. Org. Chem. 37 2001 1503 1504
22. I.V. Koval' Russ. J. Org. Chem. 38 2002 301 337 A review on N-haloimides
23. Lulinski, P.; Sosnowski, M.; Skulski, L. Paper A013 presented at the 7th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-7), Nov 1-30, 2003; http://www.mdpi.net/ecsoc-7.
24. P. Lulinski, A. Kryska, M. Sosnowski, and L. Skulski Synthesis 2004 441 445 Benzoic acid was monoiodinated in 81% yield, while nitrobenzene was unaffected
25. P. Lulinski, and L. Skulski Bull. Chem. Soc. Jpn 73 2000 951 956
26. H.O. Wirth, O. Koenigstein, and W. Kern Liebigs Ann. Chem. 634 1960 84 104 see footnote in p 90
27. Lulinski, P. Ph.D. Thesis (in Polish), Faculty of Pharmacy, Medical University of Warsaw, Poland, 2002.
28. Dictionary of Organic Compounds, 6th ed.; Chapman & Hall: London, 1996.
29. A.C. Langmuir Ber. Dtsch. Chem. Ges. 28 1895 90 96
30. E.T. Borrows, J.C. Clayton, and B.A. Hems J. Chem. Soc., (S) 1949 185 190
31. J. Arotsky, R. Butler, and A.C. Darby Chem. Commun. 1966 650
32. H.P. Burchfield, E.E. Storrs, R.J. Wheeler, V.K. Bhat, and L.L. Green Anal. Chem. 45 1973 916 920
33. A.N. Novikov, and M.G. Grigor'ev Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 20 1977 1716 1717 Chem. Abstr. 1978, 88, 89293