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Synthesis 2007(21): 3286-3289
DOI: 10.1055/s-2007-990800
DOI: 10.1055/s-2007-990800
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
A Mild and Environmentally Benign Oxidation of Thiols to Disulfides
Further Information
Received
14 September 2006
Publication Date:
21 September 2007 (online)
Publication History
Publication Date:
21 September 2007 (online)
Abstract
Thiols were effectively oxidized into disulfides by reacting with hydrogen peroxide in the presence of a catalytic amount of iodide ion or iodine.
Key words
thiol - disulfide - oxidative coupling - hydrogen peroxide - iodide catalyst
-
1a
Uemura S. In Comprehensive Organic Synthesis Vol. 7:Trost BM.Fleming I. Pergamon Press; Oxford: 1991. p.757 -
1b
Aida T.Akasaka T.Furukawa N.Oae S. Bull. Chem. Soc. Jpn. 1976, 49: 1441 -
1c
Wu X.Reike RD.Zhu L. Synth. Commun. 1996, 26: 191 -
1d
Drabowicz J.Mikolajczyk M. Synthesis 1980, 32 -
1e
Noureldine NA.Caldwell M.Hendry J.Lee DG. Synthesis 1998, 1587 -
1f
Tam JP.Wu C.-R.Liu W.Zhang J.-W. J. Am. Chem. Soc. 1991, 113: 6657 -
1g
Sanz R.Aguado R.Pedrosa MR.Arnáiz FJ. Synthesis 2002, 856 -
1h
Karimi B.Hazarkhani H.Zareyee D. Synthesis 2002, 2513 -
2a
Nagano T.Yoshikawa K.Hirobe M. Tetrahedron Lett. 1980, 21: 297 -
2b
Cervilla A.Corma A.Fornés V.Llopis E.Palanca P.Rey F.Ribera A. J. Am. Chem. Soc. 1994, 116: 1595 -
2c
Iranpoor N.Zeynizadeh B. Synthesis 1999, 49 -
2d
Kirihara M.Okubo K.Uchiyama T.Kato Y.Ochiai Y.Matsushita S.Hatano A.Kanamori K. Chem. Pharm. Bull. 2004, 52: 625 -
2e
Arisawa M.Sugata C.Yamaguchi M. Tetrahedron Lett. 2005, 46: 6907 -
3a
Price CC.Stacy GW. Org. Synth. Coll. Vol. III Wiley; New York: 1955. p.86 -
3b
Kesavan V.Bonnet-Delpon D.Bégué J.-P. Synthesis 2000, 223 - 4
Wallace TJ. J. Org. Chem. 1966, 31: 1217 -
5a
Behzad Z. J. Chem. Research, Synop. 2002, 564 -
5b
Aida T.Akasaka T.Furukawa N.Oae S. Bull. Chem. Soc. Jpn. 1976, 49: 1441 -
5c
Drabowicz J.Mikoajczyk M. Synthesis 1980, 32 -
6a
Yiannios CN.Karabinos JV. J. Org. Chem. 1963, 28: 3246 -
6b
Arterburn JB.Perry MC.Nelson SL.Dible BR.Holguin MS. J. Am. Chem. Soc. 1997, 119: 9309 - 7
Relyea DI.Tawney PO.Williams AR. J. Org. Chem. 1962, 27: 477 - 8
Shih H. J. Org. Chem. 1993, 58: 3003 - 9
The Merck Index, 13th ed.
Merck & Co., Inc.,;
Rahway:
2001.
- 10
Huang X.Chan C.-C. Synthesis 1982, 1091 - 11
Choi J.Yun NM. J. Org. Chem. 1995, 60: 3266 - 12
Lide DR. CRC Handbook of Chemistry and Physics 74th ed.: CRC Press; Ann Arbor: 1993.