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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 117, 1996 - Issue 1
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Review

RECENT ADVANCES IN THE SYNTHESIS OF SULFOXIDES FROM SULFIDES

Ernesto G. Mata Instituto de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioguímicas y Farmacéuticas. Universidad Nacional de Rosario, Casilla de Correo 991, 2000, Rosario, Argentina
Pages 231-286 | Received 31 Dec 1995, Accepted 30 Apr 1996, Published online: 24 Sep 2006

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Jürgen Voss, Dirk Otzen & Gunadi Adiwidjaja. (2017) 3,5-Thietanopentofuranoside S-oxides and S,S-dioxides – preparation and structural characterization. Phosphorus, Sulfur, and Silicon and the Related Elements 192:8, pages 919-928.
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P. Manivel, F. Nawaz Khan & VenkateshaR. Hatwar. (2010) Synthesis of Diversified Thioethers, 1-Aroylalkylisoquinolin-1-yl Thioethers, by Electrophilic S-Alkylation of 3-Phenyl Isoquinoline-1(2H)-thione. Phosphorus, Sulfur, and Silicon and the Related Elements 185:9, pages 1932-1942.
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Sergio M. Bonesi, Maurizio Fagnoni & Angelo Albini. (2008) Photosensitized electron transfer oxidation of sulfides: structure and medium effect. Journal of Sulfur Chemistry 29:3-4, pages 367-376.
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AbdolR. Hajipour, Lian-Wang Guo & ArnoldE. Ruoho. (2006) Nitric Acid in the Presence of Supported P2O5 On Silica Gel Affords an Efficient and Mild System for Oxidation of Organic Compounds Under Solvent-Free Conditions. Molecular Crystals and Liquid Crystals 456:1, pages 85-93.
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M. M. Lakouraj, M. Tajbakhsh, F. Shirini & M. V. Asady Tamami. (2005) HIO3 in the Presence of Wet SiO2: A Mild and Efficient Reagent for Selective Oxidation of Sulfides to Sulfoxides under Solvent‐Free Conditions. Synthetic Communications 35:6, pages 775-784.
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YunGui Peng, XiaoMing Feng, Xin Cui, YaoZhong Jiang, Michael C. K. Choi & Albert S. C. Chan. (2003) Catalytic Asymmetric Oxidation of Alkyl Aryl Sulfides Mediated by a Series of Chiral N-Alkyl-1,2-diphenylaminoethanol/Titanium/Water Complexes. Synthetic Communications 33:16, pages 2793-2801.
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A. R. Hajipour, S. E. Mallakpour & H. Adibi. (2002) A Selective Solid State Oxidation of Sulfides and Thiols with Benzyltriphenylphosphonium Peroxymonosulfate. Phosphorus, Sulfur, and Silicon and the Related Elements 177:10, pages 2277-2284.
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H. Firouzabadi, N. Iranpoor & R. Heydari. (2002) Application of Ionic Complex of N 2 O 4 with 18-Crown-6 as an Oxidizing Agent for the Oxidation of Organosulfur Compounds. Phosphorus, Sulfur, and Silicon and the Related Elements 177:3, pages 631-639.
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YunGui Peng, XiaoMing Feng, Xin Cui, YaoZhong Jiang & Albert S. C. Chan. (2001) CATALYTIC ASYMMETRIC OXIDATION OF SULFIDES MEDIATED BY A SERIES OF NOVEL OXAZOLINES-TITANIUM COMPLEXES. Synthetic Communications 31:15, pages 2287-2296.
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H. Firouzabadi, N. Iranpoor & R. Heydari. (2001) SILICA ACETATE COMPLEX OF N2O4: A HIGHLY EFFICIENT REAGENT FOR THE SELECTIVE CONVERSION OF THIOETHERS TO THEIR CORRESPONDING SULFOXIDES. Synthetic Communications 31:13, pages 2037-2041.
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H. Firouzabadi & M. Abbasi. (1999) Oxidation By Manganese Dioxide (mno2) Catalysed With H2SO4/silica gel. Efficient solvent-Free Oxdation Of Thioethers To Their Corresponding Sulfoxides. Synthetic Communications 29:9, pages 1485-1491.
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Attila Csaba Bényei & Laszlo Somogyi. (1998) STEREOSTRUCTURE OF ISOMERIC (±)-1-THIOFLAVANONE 1-OXIDES. Phosphorus, Sulfur, and Silicon and the Related Elements 143:1, pages 191-196.
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WilliamE. White, MicahJ. Sobus & Brianc. Okerberg. (1998) CONFORMATIONS OF MUSTARD SULFOXIDE AND MUSTARD SULFONE. Phosphorus, Sulfur, and Silicon and the Related Elements 142:1, pages 149-165.
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Crossref
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S. Lacombe, H. Cardy, M. Simon, A. Khoukh, J. Ph Soumillion & M. Ayadim. (2002) Oxidation of sulfides and disulfides under electron transfer or singlet oxygen photosensitization using soluble or grafted sensitizers. Photochemical & Photobiological Sciences 1:5, pages 347-354.
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Sandra E. Martı́n & Laura I. Rossi. (2001) An efficient and selective aerobic oxidation of sulfides to sulfoxides catalyzed by Fe(NO 3 ) 3 –FeBr 3. Tetrahedron Letters 42:41, pages 7147-7151.
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Crossref
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Ernesto G Mata. (1997) β-Lactams on Solid Support: Mild and Efficient Removal of Penicillin Derivatives from Merrifield Resin using Aluminum Chloride. Tetrahedron Letters 38:36, pages 6335-6338.
Crossref
E. G. MATA. (2010) ChemInform Abstract: Recent Advances in the Synthesis of Sulfoxides from Sulfides. ChemInform 28:34.
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