Polyvinylpyrrolidone-Supported Hydroperoxide for Selective Oxidation of Aldehydes to Carboxylic Acids and Sulfides to Sulfoxides

The facile immobilization of hydroperoxide on the cross-linked poly(vinylpyrrolidone) is described by treatment of a poly(vinylpyrrolidone)-Vilsmeier adduct with (35%) hydrogen peroxide. The in situ–generated poly(vinyl pyrrolidone)-supported hydroperoxide reagent showed very good performance in chemoselective oxidation of aldehydes to carboxylic acids as well as sulfides to sulfoxides.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Selective Oxidation of Sulfides to Sulfoxides/Sulfones by 30% Hydrogen Peroxide

Abstract

A selective and efficient procedure for the oxidation of various sulfides with sodium tungstate dihydrate with 30% hydrogen peroxide in the presence of trioctylmethylammonium dihydrogen phosphate, respectively, to the corresponding sulfoxides and sulfones is reported. The oxidation reaction is carried out at –5 to 0 °C in the presence of hydroxypropyl-β-cyclodextrins for sulfoxides or at 50–60 °C for sulfones. The mild reaction conditions, easy workup, and good yields of the products are the major advantages of this method.     

Ion Exchange Resin Catalyzed Selective Oxidation of Sulfides to Sulfoxides Using Hydrogen Peroxide

Summary. An efficient method for the selective oxidation of sulfides to sulfoxides under mild and environmentally safe conditions is achieved using hydrogen peroxide in the presence of Amberlyst 15 and Amberlite IR-400 at room temperature. This procedure can be applied for dialkyl and diaryl sulfides with a variety of functional groups. Functional groups such as hydroxyl, methoxy, amino, aldehyde, and olefinic double bonds remain intact.     

A Simple and Selective Oxidation of Sulfides to Sulfoxides Using Tetrabutylammonium Peroxydisulfate: A Rebuttal

Abstract

The report that oxidation of sulfides to sulfoxides using tetrabutylammonium peroxydisulfate (2) in methylene chloride was found to be erroneous. We repeated the procedure described in the paper and found that oxidation of sulfide to sulfoxide could not be achieved with the method.     

A Clean,Mild, and Selective Oxidation of Sulfides to Sulfoxides Using NaClO/H2SO4 in Aqueous Media

A range of sulfides can be selectively oxidized to the corresponding sulfoxides in good yields using NaClO/H₂SO₄ in both water and 50:50 water:EtOH as solvent. Two new compounds are reported that show a diastereoselective oxidation in 2-phenylthioalcohols with possible neighboring hydroxyl group participation with a logic proposed mechanism.     

Oxidation of Sulfides with Hydrogen Peroxide to Sulfoxides and Sulfones

Oxidation of sulfides with hydrogen peroxide to sulfoxides and then sulfones was studied. The conditions optimal for the formation of sulfoxides and sulfones were found.     

New Procedures for the Oxidation of Sulfides to Sulfoxides and Sulfones

New reagents for the oxidation of sulfides to the corresponding sulfoxides and sulfones are presented.     

由硫醚或亚砜氧化制砜的研究进展

对氧化硫醚或亚砜成为砜的方法作一评述,参考文献50篇.     

Microwave Thermolysis with Clayfen: Solvent-Free Oxidation of Sulfides to Sulfoxides

Alkyl, aryl and cyclic sulfides are rapidly oxidized to the corresponding sulfoxides in high yields upon microwave thermolysis with iron(III) nitrate impregnated on clay (clayfen) under solvent-free conditions; the conversion also occurs in refluxing methylene chloride but requires much longer reaction time.     

Co(acac)2催化过氧叔丁醇烯丙位与苄位氧化

以烯烃为原料,Co(acac)2为催化剂,过氧叔丁醇(t-BuO2H)为氧化剂,分别进行烯丙位与卞位氧化合成了相应的α,β-不饱和酮,其结构经1H NMR,13C NMR和Ms表征.较适宜的反应条件为:烯烃5 mmol,Co(acac)2 0.375 mmol,r-Bu0OH 25 mmol,在10 mL乙腈中,于60℃反应2 h～3 h,收率35%～96%.     

Facile and Mild Reduction of Sulfoxides to Sulfides with TiCl4/Sm System

TiCl₄/Sm system reduces sulfoxides rapidly to the corresponding sulfides in good yields in THF at room temperature.     

Selective Oxidation of Sulfides to Sulfoxides using H2O2 Catalyzed by p-Toluenesulfonic Acid (p-TsOH) Under Solvent-Free Conditions

Abstract

An efficient, chemoselective, and environmental friendly procedure for the oxidation of sulfides to sulfoxides is described. Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides in good to excellent yields using 30% H₂O₂ in the presence of catalytic amounts of a p-TsOH under solvent-free conditions at room temperature.     

Hypervalent Iodine in Synthesis XXIII: Oxidation with [Hydroxy(tosyloxy)iodo]benzene: Selective Oxidation of Sulfides to Sulfoxides

Alkyl-and aryl-sulfides can be selectively oxidated to their corresponding sulfoxides with excellent yields under mild conditions by [hydroxy (tosyloxy)iodo]benzene. Morever, [hydroxy (((+)-10-camphorosulfonyl)oxy)iodo]benzene as the chiral oxidizer, can be used to oxidate unsymmetric sulfides to sulfoxides with a few %ee to some extent.     

An Improved Method for Oxidation of Sulfides to Sulfoxides with Hydrogen Peroxide in Methanol

A variety of oxidative methods have been used for the preparation of sulfoxides from the corresponding sulfides². However, only few of them permit the oxidation in a selective manner. These methods involve for example sodium metaperiodate³, dichloroiodobenzene⁴ and t-butyl hypochlorite⁵ as oxidising agent. It should be noted that it is necessary to use them in equivalent amounts in respect to sulfide in order to avoid the over-oxidation or α-halogenation reaction.