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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 6
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Original Articles

HIO3 in the Presence of Wet SiO2: A Mild and Efficient Reagent for Selective Oxidation of Sulfides to Sulfoxides under Solvent‐Free Conditions

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Pages 775-784 | Received 10 Jun 2004, Published online: 20 Aug 2006

References

  • Patai , S. , Roppoport , Z. and Stirling , C. 1988 . The Chemistry of Sulfones and Sulfoxides Edited by: Patai , S. , Roppoport , Z. and Stirling , C. Chichester : John Wiley & Sons .
  • Block , E. 1978 . Reaction of Organosulfur Compounds New York : Academic Press .
  • Hudlicky , M. 1990 . Oxidations in Organic Chemistry 252 Washington, D.C. : ACS .
  • Mata , E. G. 1996 . Recent advances in the synthesis of sulfoxides from sulfides . Phosphorus, Sulfur, and Silicon , 117 : 231
  • Hirano , M. , Kudo , H. and Morimot , T. 1994 . Zeolite‐assisted oxidation of sulfides with sodium bromide trihydrate in aprotic solvents . Bull. Chem. Soc. Jpn. , 67 ( 5 ) : 1492
  • Oae , S. 1977 . Organic Chemistry of Sulfur Edited by: Oae , S. New York : Plenum Press . Ch. 8
  • Drabowicz , J. , Kielbasinki , P. and Mikolajczyk , M. 1994 . The Synthesis of Sulphones, Sulphoxides and Cyclicsulphides Edited by: Patai , S. and Rappoport , Z. Sussex, , England : John Wiley & Sons . Ch. 3
  • Song , G. , Wang , F. , Zang , H. , Lu , X. and Wang , C. 1998 . Efficient oxidation of sulfides catalyzed by transition metal salts with molecular oxygen in the presence of aldehydes . Synth. Commun. , 28 ( 15 ) : 2783 – 2787 .
  • Barton , D. H. R. , Li , W. and Smith , J. A. 1998 . Binuclear manganes complexes as catalysts in the selective and efficient oxidation of sulfides to sulfoxides . Tetrahedron Lett. , 39 : 7055 – 7058 .
  • Folsom , H. E. and Castrillon , J. 1992 . The controlled oxidation of organic sulfides to sulfoxides with the help of o‐iodosylbenzoic acid . Synth. Commun. , 22 ( 12 ) : 1799 – 1806 .
  • Hashmat , A. M. 1998 . A Simple and efficient procedure for oxidation of sulfides to sulfoxides on hydrated silica gel with ceric ammonium nitrate (CAN) in methylene chloride . Synth. Commun. , 28 ( 16 ) : 2969 – 2981 .
  • Martin , S.E. and Rossi , L. I. 2001 . An efficient and selective aerobic oxidation of sulfides to sulfoxides catalyzed by Fe(NO3)3‐FeBr3 . Tetrahedron Lett. , 42 : 7147 – 7151 .
  • Hajipour , A. R. , Mallakpour , S. E. and Adibi , H. 2002 . Selective and efficient oxidation of sulfides and thiols with benzyl triphenylphosphonium peroxymonosulfate in aprotic solvent . J. Org. Chem. , 67 : 8666 – 8668 .
  • Yamazaki , S. 1996 . Effects of exogenous IL‐2 ontolerance induction by anti‐ICAM‐1 and anti‐LFA‐1 monoclonal antibodies . Bull. Chem. Soc. Jpn. , 69 : 2955
  • Hirano , M. , Komiya , K. , Yakabe , S. , Clark , J. H. and Morimoto , T. 1996 . A selective and convenient oxidation of sulfides to sulfoxides with ferric nitrate and silica gel . Org. Prep. Proced. Int. , 28 ( 6 ) : 705
  • Arterburn , J. B. and Nelson , S. L. 1996 . Rhenium‐catalyzed oxidation of sulfides with phenyl sulfoxides . J. Org. Chem. , 61 : 2260 – 2261 .
  • Bosch , E. and Kochi , J. K. 1995 . Selective catalysis of thioether oxidations with dioxygen critical role of nitrosonium EDA complexes in the thermal and photochemical transfer of oxygen from nitrogen oxides to sulfur centers . J. Org. Chem. , 60 : 3172 – 3183 .
  • Aldea , R. and Alper , H. 1995 . Selective aerobic oxidation of sulfides using a novel palladium complex as the catalyst precursor . J. Org. Chem. , 60 : 8365 – 8366 .
  • Suerez , A. R. , Rossi , L. L. and Martin , S. E. 1995 . Oxidation of organic sulphides to sulphoxides by nitric acid catalyzed by FeBr3 and (FeBr3)2 (DMSO)3 . Tetraheron Lett. , 36 ( 8 ) : 1201 – 1204 .
  • Webb , K. S. 1994 . A mild, inexpensive and practical oxidation of sulfides . Tetrahedron Lett. , 35 ( 21 ) : 3457 – 3460 .
  • Siedlecka , R. and Skarzewski , J. 1994 . Facial oxidation of sulfides to sulfoxides using sodium hypochlorite and oxoammonium salt as a catalyst: Chemo‐ and diasteroselective transformation of bis(phenylthio)alkanes into sulfoxides . Synthesis , 4 : 401 – 404 .
  • Adam , W. , Mitchell , C. M. and Saha‐Meller , C. R. 1994 . Chemoselective methyltrioxo rhenium(VII)‐catalyzed sulfoxidations with hydrogen peroxide . Tetrahedron , 50 ( 46 ) : 13121 – 13124 .
  • DesMarteau , D. D. , Petrov , V. A. , Montanari , V. , Pregnolato , M. and Resnati , G. 1994 . Mild and selective oxygenation of sulfides to sulfoxides and sulfones by perfluoro‐cis‐2,3‐dialkyloxaziridines . J. Org. Chem. , 59 ( 10 ) : 2762
  • Fringuelli , F. , Pellegrino , P. and Pizzo , F. 1993 . Facile and selective oxidation of sulfides to sulfoxides by t‐butylhydroperoxide in aqueous medium . Synth. Commun. , 23 ( 22 ) : 3157
  • Page , P. C. B. , Graham , A. E. , Bethell , D. and Park , B. K. 1993 . A simple and convenient method for oxidation of sulphides . Synth. Commum. , 23 ( 11 ) : 1507
  • Ramkumar , D. and Sankararaman , S. 1993 . Selective photooxidation of sulfides to sulfoxides with tetranitromethane . Synthesis , 11 : 1057 – 1058 .
  • Balicki , R. , Kaczmarek , L. and Nantka‐Namirski , P. 1992 . A mild and facile preparation of sulfoxides from sulfides by use of the H2O2‐urea/phthalic anhydride system . Liebigs Ann. Chem. , 8 : 883
  • Gasparrini , F. , Giovannoli , M. , Misiti , D. , Natile , G. and Palmieri , G. 1990 . A general procedure for the selective oxidation of sulfides to sulfoxides by nitric acid: Tetrabromoaurate(II) catalyst in a biphasic system . J. Org. Chem. , 55 : 1323 – 1328 .
  • Kim , K. S. , Hwang , H. J. , Cheong , C. S. and Hahn , C. S. 1990 . Tellurium dioxide catalyzed selective oxidation sulfides to sulfoxides with hydrogen peroxide . Tetrahedron Lett. , 31 ( 20 ) : 2893 – 2894 .
  • Toda , F. 1995 . Solid state organic chemistry: Efficient reactions, remarkable yields, and stereoselectivity . Acc. Chem. Res. , 28 ( 12 ) : 480
  • Tanda , K. and Toda , F. 2000 . Solvent‐free organic synthesis . Chem. Rev. , 100 : 1025 – 1074 .
  • Varma , R. S. and Dahiya , R. 1998 . Microwave thermolysis with clayfen: Solvent‐free oxidation of sulfides to sulfoxides . Synth. Commun. , 28 ( 21 ) : 4087 – 4095 .
  • Firouzabadi , H. , Iranpoor , N. and Zolfigol , M. A. 1998 . Dinitrogen tetroxide complexes of iron(III) and copper(II) nitrates as new versatile reagents for organic synthesis: Efficient and selective oxidation of sulfides to their corresponding sulfoxides under mild conditions . Synth. Commun. , 28 ( 2 ) : 377 – 385 .
  • Shirini , F. , Zolfigol , M. A. and Azadbar , M. R. 2002 . Efficient solvent‐free deoximation and dehydrazonation with HIO3 in the presence of wet SiO2 . Synth. Commun. , 32 ( 3 ) : 315 – 318 .
  • Shirini , F. , Zolfigol , M. A. , Lakouraj , M. M. and Azadbar , M. R. 2001 . Efficient oxidation of sulfides to sulfoxides and of thiols to disulfides with aqueous HIO3 . Russ. J. Org. Chem. , 37 ( 9 ) : 1405 – 1406 .
  • Lakouraj , M. M. , Movassagh , B. and Ghodrati , K. 2002 . Caros and supported on silica gel IV: Facile synthesis of sulfones by the oxidation of various sulfides in aprotic solvent . Synth. Commun. , 32 ( 6 ) : 847 – 850 .
  • 1966 . Dictionary of Organic Compounds , 6th Ed. London : Chapman & Hall .
  • Orito , K. , Hatakeyama , T. , Takeo , M. and Suginome , H. 1995 . Oxidation with mercury(II) oxide‐iodine reagent: selective oxidation of sulfides to sulfoxides . Synthesis , 11 : 1357 – 1358 .
  • 1989–1990 . Handbook of Chemistry and Physics , 70th Ed. USA : CRC Press .
  • Fabretti , A. , Ghelfi , F. , Grandi , R. and Pagnoni , U. M. 1994 . Sulfoxides from thioethers and MnO2–HCl . Synth. Commun. , 24 ( 17 ) : 2393 – 2398 .
  • Babieri , G. , Cinquini , M. , Colonna , S. and Montanari , F. 1968 . Reaction of sulfides with iodobenzene dichloride in aq. pyridine‐synthesis of sulfoxides free from sulfone and 18o‐labeled sulfoxides . J. Chem. Soc. C , : 659
  • Tsuchiya , Y. , Mori , M. , Taguchi , T. and Yakugaku , Z. 1976 . Reactions of 2‐[alkyl (or aryl) sulfinyl ethanol and their related compounds with carbon disulfide: formation of trithiocarbonates and its mechanistic consideration . 96 : 490 [Chem. Abstr. 1976, 85, 142216]
  • 1990–91 . Aldrich Catalog Handbook of Fine Chemicals Aldrich Co. .
  • 1990–91 . Fluka, Chemika‐Biochemika Fluka Chemie AG .
  • Liu , K. T. and Tong , Y. C. 1978 . Oxidation with supported oxidations, 2: Preparation of sulfoxides by alumina‐supported sodium metaperiodate . J. Org. Chem. , 43 ( 13 ) : 2717 – 2718 .
  • Firouzabadi , H. and Abbasi , M. 1991 . Conversion of sulfides to their corresponding sulfoxides with barium permanganate Ba(MnO4)2 under non‐aqueous condition . Synth. Commun. , 21 ( 2 ) : 211
  • Firouzabadi , H. , Iranpour , N. and Zolfigol , M. A. 1998 . Selective and efficient transformation of thioethers to their sulfoxides and catalytic conversion of thiols to the disulfides with hydrate iron(III) and copper(II) nitrates in aprotic organic solvents or under solvent‐free conditions . Synth. Commun. , 28 : 1179 – 1187 .
  • Varma , R. S. , Saini , R. K. and Meshram , H. M. 1997 . Selective oxidation of sulfides to sulfoxides and sulfones by microwave thermolysis on wet silica‐supported sodium periodates . Tetrahedron Lett. , 38 ( 37 ) : 6525 – 6528 .
  • Varma , R. S. 1998 . Selective oxidations using alumina‐supported iodobenzene diacetate under solvent‐free conditions . J. Chem. Res. , : 120 – 121 .
  • Varma , R. S. and Dahiya , R. 1998 . Microwave thermolysis with clayfen: solvent‐free oxidation of sulfides to sulfoxides . Synth. Commun. , 28 ( 21 ) : 4087 – 4095 .
  • Lakouraj , M. M. , Movassagh , B. and Fadaei , Z. 2002 . Synthesis of organic sulfides via Zn/AlCl3 system in aqueous media . Synth. Commun. , 32 ( 8 ) : 1237 – 1242 .
  • Kim , S. S. , Kim , D. W. and Jung , H. C. 2002 . A mild and highly efficient oxidation of sulfides to sulfoxides with periodic acid catalyzed by FeCl3 . Synthesis , 17 : 2484 – 2486 .
  • Varma , R. S. 1998 . Selective oxidations using alumina‐supported iodobenzene diacetate under solvent‐free conditions . J. Chem. Res. , : 120 – 121 .
  • Mashraqui , S. H. 1998 . Bi(NO3)3 · 5H2O: A convenient reagent for selective oxidation of sulfides to sulfoxides . Synth. Commun. , 28 ( 6 ) : 939 – 943 .
  • Choudary , B. M. , Bharathi , B. , Reddy , C. V. and Kantam , M. L. 2002 . The first example of catalytic n‐oxidation of tertiary amines by tungstate‐exchanged Mg‐Al layered double hydroxide in water: a green protocol . J. Chem. Soc., Perkin Trans. 1 , : 2069 – 2074 .
  • Szarek , W. A. , Vyas , D. M. , Sepulchre , A.‐M. , Gero , S. D. and Luckacs , G. 1974 . Carbon‐13 nuclear magnetic resonance spectra of 1,4‐oxathiane derivatives . Can. J. Chem. , 52 : 2041

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