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Synthesis 2005(1): 22-24
DOI: 10.1055/s-2004-834873
DOI: 10.1055/s-2004-834873
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Selective Oxidation of Sulfides to Sulfoxides Using IBX-Esters
Further Information
Received
19 July 2004
Publication Date:
21 October 2004 (online)
Publication History
Publication Date:
21 October 2004 (online)
Abstract
IBX-esters (esters of 2-iodoxybenzoic acid) are convenient hypervalent iodine reagents for the clean and selective oxidation of organic sulfides to sulfoxides. This reaction proceeds without over-oxidation to sulfones and is compatible with the presence of the hydroxy group, double bond, phenol ether, benzylic carbon, and various substituted phenyl rings in the molecule of the substrate.
Key words
hypervalent iodine - IBX-esters - sulfides - sulfoxides
-
1a
Block E. Angew. Chem., Int. Ed. Engl. 1992, 31: 1135 -
1b
Holland HL. Chem. Rev. 1988, 88: 473 -
2a
Hudlicky M. Oxidations in Organic Chemistry Washington, DC; American Chemical Society: 1990. -
2b
Procter DJ. J. Chem. Soc., Perkin. Trans. 1 1999, 641 -
2c
Madesclaire M. Tetrahedron 1986, 42: 5459 -
3a
Varvoglis A. The Organic Chemistry of Polycoordinated Iodine VCH Publishers Inc.; New York: 1992. -
3b
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997. -
3c
Hypervalent Iodine Chemistry, In Topics in Current Chemistry
Vol. 224:
Wirth T. Springer-Verlag; Berlin Heidelberg: 2003. -
3d
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
3e
Wirth T.Hirt UH. Synthesis 1999, 1271 -
4a
Tohma H.Takizawa S.Watanabe H.Kita Y. Tetrahedron Lett. 1998, 39: 4547 -
4b
Tohma H.Maegawa T.Kita Y. ARKIVOC 2003, 6: 62 -
4c
Tohma H.Takizawa S.Watanabe H.Fukuoka Y.Maegawa T.Kita Y. J. Org. Chem. 1999, 64: 3519 -
4d
Tohma H.Takizawa S.Morioka H.Maegawa T.Kita Y. Chem. Pharm. Bull. 2000, 48: 445 -
4e
Shukla VG.Salgaonkar PD.Akamanchi KG. J. Org. Chem. 2003, 68: 5422 -
4f
Ochiai M.Nakanishi A.Ito T. J. Org. Chem. 1997, 62: 4253 -
4g
Ray DG.Koser GF. J. Org. Chem. 1992, 57: 1607 -
4h
Koser GF.Kokil PB.Shah M. Tetrahedron Lett. 1987, 28: 5431 -
4i
Xia M.Chen Z. Synth. Commun. 1997, 27: 1315 -
4j
Ou W.Chen Z. Synth. Commun. 1999, 29: 4443 -
4k
Yang R.Dai L. Synth. Commun. 1994, 24: 2229 -
4l
Barton DHR.Godfrey CRA.Morzycki JW.Motherwell WB.Stobie A. Tetrahedron Lett. 1982, 23: 957 -
4m
Barbieri G.Cinquini M.Colorina S.Montanari F. J. Chem. Soc., C 1968, 659 - 5
Zhdankin VV.Litvinov DN.Koposov AY.Luu T.Ferguson MJ.McDonald R.Tykwinski RR. J. Chem. Soc., Chem. Commun. 2004, 106 -
6a
Kutchin AV.Rubtsova SA.Loginova IV. Izv. Akad. Nauk Ser. Khim. 2001, 50: 413 -
6b
Ali MH.Stevens WC. Synthesis 1997, 764 -
6c
Batigalhia F.Zaldini-Hernandes M.Ferreira AG.Malvestiti I.Cass QB. Tetrahedron 2001, 57: 9669 -
6d
Yamamoto T.Kakimoto M.Okawara M. Bull. Chem. Soc. Jpn. 1979, 52: 841 -
6e
Yang Y.Szafraniec LL.Beaudry WT. J. Org. Chem. 1990, 55: 3664