RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(5): 690-692
DOI: 10.1055/s-2008-1032165
DOI: 10.1055/s-2008-1032165
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Direct Synthesis of Iodoarenes from Aromatic Substrates Using Molecular Iodine
Weitere Informationen
Received
3 October 2007
Publikationsdatum:
08. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
08. Februar 2008 (online)
Abstract
Easy laboratory procedures for oxidative iodination of aromatic substrates are presented. One procedure includes the iodination using molecular iodine, concentrated sulfuric acid, and potassium peroxodisulfate, and another uses a reagent system containing molecular iodine, potassium peroxodisulfate, and trifluoroacetic acid. These procedures are especially effective for benzene and less deactivated aromatic substrates, such as halobenzenes, trifluoromethylbenzene, and benzoic acid.
Key words
arenes - molecular iodine - iodoarenes - iodination - potassium peroxodisulfate
- Reviews on aromatic iodination:
-
1a
Roedig A. In Houben-Weyl, Methoden der organischen Chemie 4th ed., Vol. 5/4:Mueller E. Thieme; Stuttgart: 1960. p.517 -
1b
Merkushev EB. Usp. Khim. 1984, 53: 583 ; Russ. Chem. Rev. (Engl. Transl.); 1984, 53, 343 -
1c
Merkushev EB. Synthesis 1988, 923 -
1d
Sasson Y. In The Chemistry of Halides, Pseudohalides and Azides, Suppl. D1Patai S.Rappoport Z. Wiley-Interscience; Chichester: 1995. p.535 -
1e
Steel PG. In Rodd’s Chemistry of Carbon Compounds, Part 1 2nd ed., Vol. 3:Sainsbury M. Elsevier; Amsterdam: 1996. p.178 - 2
Krassowska-Swiebocka B.Lulinski P.Skulski L. Synthesis 1995, 926 - 3
Lulinski P.Skulski L. Bull. Chem. Soc. Jpn. 1997, 70: 1665 - 4
Lulinski P.Skulski L. Bull. Chem. Soc. Jpn. 1999, 72: 115 - 5
Shimizu A.Yamataka K.Isoya T. Bull. Chem. Soc. Jpn. 1985, 58: 1611 - 6
Lulinski P.Skulski L. Bull. Chem. Soc. Jpn. 2000, 73: 951 - 7
Kryska A.Skulski L. J. Chem. Res., Synop. 1999, 590 - 8
Barluenga J.Campos PJ.González JM.Asensio G. Chem. Soc., Perkin Trans. 1 1984, 2623 - 9
Agnieszka ZA.Skulski L. Molecules 2005, 10: 1307 - 10
Sathiyapriya R.Karunakaran RJ. E-J. Chem. 2006, 3: 65 - 11
Yang SG.Kim YH. Tetrahedron Lett. 1999, 40: 6051 - 12
Noda Y.Kashima M. Tetrahedron Lett. 1997, 38: 6225 - 13
Rozen S.Zamir D. J. Org. Chem. 1990, 55: 3552 - 14
Shellhamer DF.Jones BC.Pettus BJ.Pettus TL.Stringer JM.Heasley VL. J. Fluorine Chem. 1998, 88: 37 - 15
Zupan M.Iskra J.Stavber S. Tetrahedron Lett. 1997, 38: 6305 - 16
Bradzil LC.Cutler CJ. J. Org. Chem. 1994, 59: 6233 - 17
Sy W.-W. Tetrahedron Lett. 1993, 34: 6223 - 18
Bachky A.Foubelo F.Yus M. Tetrahedron 1994, 50: 5139 - 19
Hossain MD.Kitamura T. Tetrahedron Lett. 2006, 47: 7889 - 20
Hossain MD.Ikegami Y.Kitamura T. J. Org. Chem. 2006, 71: 9903 - 21
Lulinski P.Kryska A.Sosnowski M.Skulski L. Synthesis 2004, 441 - 22 Dictionary of Organic Compounds 6th ed.: Chapman & Hall; London: 1996.
- 23
Lulinski P.Krassowska-Swiebocka B.Skulski L. Molecules 2004, 9: 595