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DOI: 10.1055/s-0029-1217180
Iodoxybenzene (PhIO2)
Publikationsverlauf
Publikationsdatum:
18. Mai 2009 (online)
Biographical Sketches
![](https://www.thieme-connect.de/media/synlett/200909/v284_zhang.jpg)
Introduction
Iodoxybenzene (PhIO2, mp 230 ˚C) is the first organic compound of iodine(V) prepared by Willgerodt 100 years ago. [¹] Specifically, it can be prepared by disproportionation of iodosylbenzene under steam distillation. [²] Ten years ago iodoxybenzene has been used for the synthesis of cadalenquinone, [³a] unsaturated carbonyl compounds [³b-c] , oxodienes, [³d-e] , epoxides, [³f] quinine imines, [³g] and sulfones. [³h] In this Spotlight recent applications using PhIO2 in organic syntheses are summarized.
Preparation
Iodoxybenzene (PhIO2) can be directly prepared using commercial 40% peracetic acid or sodium periodate by dissolving iodobenzene in water (Scheme [¹] ). [4]
![](https://www.thieme-connect.de/media/synlett/200909/v284_s1.gif)
Scheme 1
Abstracts
(A) Kita et al. show the solubilization and activation of PhIO2 by adding catalytic amounts of both cetyltrimethylammonium bromide (CTAB) or MgBr2 and a chiral tartaric acid derivative. Both reagents were indispensable for the enhancement of chemical and optical yields in the oxidation of sulfides to sulfoxides. [5] |
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(B) The application of PhIO2 in the oxidation reaction of phosphorous, phosphorothiono and phosphoroseleno compounds into the corresponding ºP(O) analogues was demonstrated by Lopusinski et al. [6a] The direct conversion of ammonium dialkyl phosphoroselenoates into the dialkyl phosphoramidates using iodoxybenzene has been developed by the same group. [6b] |
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(C) The reaction performed between N-sulfinylphosphoramidate and PhIO2 in the presence of diethylphosphoramidate results in the formation of N,N-bis(diethylphosphor)sulfamide. [7] |
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(D) Catalytic allylic oxidation of alkenes into enones and oxidation of aryl alkyl ketones into the corresponding ketoacids with a fluorous seleninic acid as catalyst in conjunction with PhIO2 as reoxidant have been developed by Zou and co-worker. [8] |
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(E) Recently, air-driven conversion of alcohols into carbonyl compounds in water using catalytic amounts of PhIO2 has been reported by Liu and co-workers. [9] |
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- 1
Willgerodt C. Die Organischen Verbindungen mit Mehrwertigem Jod Enke Verlag; Stuttgart: 1914. - 2
Willgerodt C. J. Prakt. Chem. 1886, 33: 154 -
3a
Reddy N.Kesavulu Rao.G SK. Indian J. Chem., Section B: Org, Chem. Incl. Med. Chem. 1987, 26B: 920 -
3b
Barton DHR.Crich D. Tetrahedron 1985, 41: 4359 -
3c
Gleiter R.Mueller G. J. Org. Chem. 1988, 53: 3912 -
3d
Künzer H.Sauer G.Wiechert R. Tetrahedron 1989, 45: 6409 -
3e
Iida T.Nishida S.Chang FC.Niwa T.Goto J.Nambara T. Chem. Pharm. Bull. 1993, 41: 763 -
3f
Barret R.Sabot JP.Pautet F.Cerf P.Daudon M. Oxidation Communications 1989, 12: 55 -
3g
Barret R.Daudon M. 1990, 20: 1543 -
3h
Barret R.Pautet F.Bordat P.Tinland B.Daudon M. Phosphorus, Sulfur and Silicon and the Related Elements 1989, 45: 31 -
4a
Sharefkin JG.Saltzman H. Org. Synth. 1963, 43: 65 -
4b
Kazmierczak P.Skulski L.Kraszkiewicz L. Molecules 2001, 6: 881 -
5a
Tohma H.Takizawa S.Watanabe H.Fukuoka Y.Maegawa T.Kita Y. J. Org. Chem. 1999, 64: 3519 -
5b
Tohma H.Takizawa S.Morioka H.Maegawa T.Kita Y. Chem. Pharm. Bull. 2000, 48: 445 -
6a
Mielniczak G.Lopusinski A. Synlett 2001, 505 -
6b
Mielniczak G.Lopusinski A. Heteroatom Chem. 2003, 14: 121 - 7
Mielniczak G.Lopusinski A. Heteroatom Chem. 2008, 19: 530 -
8a
Crich D.Zou Y. Org. Lett. 2004, 6: 775 -
8b
Crich D.Zou Y. J. Org. Chem. 2005, 70: 3309 - 9
Mu RZ.Liu ZQ.Yang ZJ.Liu ZG.Wu LM.Liu ZL. Adv. Synth. Catal. 2005, 347: 1333
References
- 1
Willgerodt C. Die Organischen Verbindungen mit Mehrwertigem Jod Enke Verlag; Stuttgart: 1914. - 2
Willgerodt C. J. Prakt. Chem. 1886, 33: 154 -
3a
Reddy N.Kesavulu Rao.G SK. Indian J. Chem., Section B: Org, Chem. Incl. Med. Chem. 1987, 26B: 920 -
3b
Barton DHR.Crich D. Tetrahedron 1985, 41: 4359 -
3c
Gleiter R.Mueller G. J. Org. Chem. 1988, 53: 3912 -
3d
Künzer H.Sauer G.Wiechert R. Tetrahedron 1989, 45: 6409 -
3e
Iida T.Nishida S.Chang FC.Niwa T.Goto J.Nambara T. Chem. Pharm. Bull. 1993, 41: 763 -
3f
Barret R.Sabot JP.Pautet F.Cerf P.Daudon M. Oxidation Communications 1989, 12: 55 -
3g
Barret R.Daudon M. 1990, 20: 1543 -
3h
Barret R.Pautet F.Bordat P.Tinland B.Daudon M. Phosphorus, Sulfur and Silicon and the Related Elements 1989, 45: 31 -
4a
Sharefkin JG.Saltzman H. Org. Synth. 1963, 43: 65 -
4b
Kazmierczak P.Skulski L.Kraszkiewicz L. Molecules 2001, 6: 881 -
5a
Tohma H.Takizawa S.Watanabe H.Fukuoka Y.Maegawa T.Kita Y. J. Org. Chem. 1999, 64: 3519 -
5b
Tohma H.Takizawa S.Morioka H.Maegawa T.Kita Y. Chem. Pharm. Bull. 2000, 48: 445 -
6a
Mielniczak G.Lopusinski A. Synlett 2001, 505 -
6b
Mielniczak G.Lopusinski A. Heteroatom Chem. 2003, 14: 121 - 7
Mielniczak G.Lopusinski A. Heteroatom Chem. 2008, 19: 530 -
8a
Crich D.Zou Y. Org. Lett. 2004, 6: 775 -
8b
Crich D.Zou Y. J. Org. Chem. 2005, 70: 3309 - 9
Mu RZ.Liu ZQ.Yang ZJ.Liu ZG.Wu LM.Liu ZL. Adv. Synth. Catal. 2005, 347: 1333
References
![](https://www.thieme-connect.de/media/synlett/200909/v284_s1.gif)
Scheme 1
![](https://www.thieme-connect.de/media/synlett/200909/v284_s2.gif)
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![](https://www.thieme-connect.de/media/synlett/200909/v284_s5.gif)
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