Synthesis of 3-Coumaryl Phenyl Sulfones or Sulfoxides

An unambiguous synthesis of a number of 3-coumaryl phenyl sulfones or sulfoxides have been described which were obtained by the oxidation of the corresponding sulfides with hydrogen peroxide. The sulfides were prepared by the Perkin-Oglialore reaction of o-hydroxyaldehyde with the sodium salt of different S-phenyl thioacetic acids. The sulfones did not exhibit any appreciable antitubercuious activity in the preliminary screening tests.     

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.     

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.     

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.     

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.     

Reactions of Sulfenyl,Sulfinyl, and Sulfonyl Halides with Conjugated Dienes and Enynes. Synthesis of Unsaturated Sulfides,Sulfoxides, and Sulfones

The reactivities of sulfenyl, sulfinyl, sulfonyl halides in additions to conjugated dienes'enynes, and their derivatives are compared. Despite the fact that all these reactions involve cleavage offormally similar S-Cl bonds, the addition direction and rate depend on the structure of the reactants (dienes and enynes; organosulfur acid chlorides).     

Alkatrienyl Sulfoxides and Sulfones. Part I. 3-Methyl-1,2,4-pentatrienyl Phenyl Sulfoxide-Synthesis and Electrophile-Induced Cyclization Reactions

A method for the synthesis of the 3-methyl-1,2,4-pentatrienyl phenyl sulfoxide 3 by [2,3]-sigmatropic rearrangement of the 3-methyl-1-penten-4-yn-3-yl benzenesulfenate 2 , formed in the reaction of the 3-methyl-1-pentene-4-yn-2-ol 1 with phenylsulfenyl chloride has been created. Possibilities and restrictions of the five-membered heterocyclization in electrophile-induced reactions leading to the synthesis of the 5H-1,2-oxathiol-2-ium salts 5 , 7 , and 8 have been explored. Chlorination of the sulfoxide 2 proceeded with formation of the (E)-2-chloro-3-methylene-1,4-pentadienyl phenyl sulfoxide 4 , while the bromination afforded the 4-bromo-5H-1,2-oxathiol-2-ium bromide 5 , which after reflux in 1,2-dichloroethane eliminated hydrogen bromide and was transformed into the (E)-2-bromo-3-methylene-1,4-pentadienyl phenyl sulfoxide 6 .     

Electrochemical Fluorination of Unsaturated Sulfides and Sulfones

Electrochemical fluorination of some unsaturated sulfides and sulfones and their reactions with anhydrous HF were studied.     

硫化物的生物氧化成手性亚砜

描述了硫化物不对称生物氧化成手性亚砜, 主要为氯过氧化物酶、环己酮单氧酶催化有机硫化物氧化成具有光学活性的亚砜的两条酶促反应途径.     

Cyclopropanation of Vinyl Sulfides and Vinyl Sulfones

Cyclopropanation of vinyl sulfones and vinyl sulfides can be achieved by phase transfer catalysis where other cyclopropanation methods have failed.     

Diastereocontrolled Synthesis of Cyclopropane Phenyl Sulfoxides

Good diastereocontrol of three stereocentres is obtained in the synthesis of cyclopropane pheny¹ sulfoxides.     

1,2-联烯亚砜和1,2-联烯砜的反应

1,2-联烯亚砜和1,2-联烯砜是重要的含硫联烯化合物.综述了1,2-联烯亚砜和1,2-联烯砜的亲核加成、亲电加成、Diels-Alder反应、1,3-偶极加成、[2+2]环加成等反应以及在天然产物中的应用.     

One-Pot Synthesis of α-Methyl Vinyl Sulfones From Ethyl Phenyl Sulfones

Various α-methyl vinyl sulfones were synthesized by Homer-Emmons olefination of aldehydes and sulfonyl phosphonate generated from 1,1-dilithiosulfone.     

Sulfonated Condensed Polynuclear Aromatic (S-Copna) Resin Catalyzed Selective Oxidation of Sulfides to Sulfoxides or Sulfones Using Hydrogen Peroxide

Abstract

Sulfonated condensed polynuclear aromatic (S-COPNA) resin was found to be a highly efficient, environmentally friendly, recyclable heterogeneous catalyst for the oxidation of alkyl and aryl sulfides to the corresponding sulfoxides or sulfones, in good yields under mild reaction conditions using 30% hydrogen peroxide as an oxidant.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Synthesis of the S-COPNA resin catalyst. Spectroscopic data for compounds.     

A Convenient Procedure for the Reduction of Sulfones to Sulfoxides

Although there have been a relatively large number of publications recently dealing with the reduction of sulfoxides fo sulfides^1,2 there are still very few general procedures for the reduction of sulfones to sulfides and none at all, as far as we are aware, for the reduction of sulfones to sulfoxides. In his paper dealing with the use of diisobutylaluminum hydride (DIBAL-H) for the reduction of sulfones to sulfides, for example, Gardner³ points out the inadequacies of the more readily available lithium aluminum hydride for this reduction. We have developed a two part procedure for reducing sulfones 1 to sulfoxides 2 which fills an important gap in the functional group interconversion of organosulfur compounds, the results of which we now describe.     

Evidence of Two Key Intermediates Contributing to the Selectivity of P450‐Biomimetic Oxidation of Sulfides to Sulfoxides and Sulfones

A mild process for the selective oxidation of sulfides is in great demand. Therefore, probing the mechanism underlying the biological oxidation of sulfides under ambient conditions may provide valuable insights for the development of such a reaction. Based on porphyrin models of P450 enzymes, evidence of two key intermediates, Int0 and Int1 , in this reaction is provided. Spectroscopic studies indicated the formation of a hydroperoxide‐iron(III) species ( Int0 ) upon addition of H₂O₂. This intermediate proved to be highly selective for sulfoxide production. By contrast, a defined porphyrin oxoiron(IV) cation radical ( Int1 ) directly reacted with sulfoxides, leading selectively to the corresponding sulfones. Interestingly, the available sulfoxides reversibly act as a new axial ligand for Int0 forming a more active species Int0 _SO. The amount of Int0 increased in the presence of alkyl, aryl, or aromatic sulfides, while Int1 formed in the absence of these sulfides. Thus, sulfoxides and sulfones would selectively form under conditions that favor the corresponding intermediates, which elucidate the biological oxidation pathway.