Oxidation of organic compounds by zinc permanganate

Wolfe, Saul; Ingold, Christopher F.

doi:10.1021/ja00364a054

Cited by 74 publications

(23 citation statements)

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“…[38] Several methods for the oxidation of alkynes are described in the literature involving different types of reagents such as metal-containing oxidants, [39] hydrogen peroxide catalyzed by metal complexes, [40,41] [fluoro-(trifluoromethylsulfonyloxy)iodo]benzene [42] and dimethyldioxirane, [43] each used for a specific substrate. [38] Several methods for the oxidation of alkynes are described in the literature involving different types of reagents such as metal-containing oxidants, [39] hydrogen peroxide catalyzed by metal complexes, [40,41] [fluoro-(trifluoromethylsulfonyloxy)iodo]benzene [42] and dimethyldioxirane, [43] each used for a specific substrate.…”

Section: Unique Epoxidationsmentioning

confidence: 99%

“…The action of HOF·CH 3 CN on the π-centers of acetylenes was also studied. [38] Several methods for the oxidation of alkynes are described in the literature involving different types of reagents such as metal-containing oxidants, [39] hydrogen peroxide catalyzed by metal complexes, [40,41] [fluoro-(trifluoromethylsulfonyloxy)iodo]benzene [42] and dimethyldioxirane, [43] each used for a specific substrate. All these procedures have apparently a common mechanism that involves a formation of oxirene A which, although never isolated, was assumed to be the first step.…”

Section: Unique Epoxidationsmentioning

confidence: 99%

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Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Rozen

2005

Eur J Org Chem

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At present, HOF·CH3CN complex is the best oxygen transfer agent that chemistry has to offer. It is readily made by passing dilute fluorine through aqueous acetonitrile and does not require any isolation or purification. It is stable in aqueous acetonitrile solution for a few hours at room temperature, providing ample opportunities for various reactions. Epoxidation of regular olefins as well as of very electron‐depleted ones proceeds smoothly. HOF·CH3CN transfer oxygen also to heteroatoms, especially sulfur and nitrogen. Even very electron‐depleted sulfides such as RfSAr that are very difficult to oxidize, are converted into the respective sulfones in a matter of minutes. On the other hand, since the reaction conditions are very mild, the reagent can oxidize various thiophenes and amino acids to the corresponding S,S‐dioxides and α‐nitro acid derivatives. HOF·CH3CN was also instrumental in ending the 50 years quest for making the elusive 1,10‐phenanthroline N,N‐dioxide and for the novel transformation of azides to nitro derivatives. The use of BrF3 for making symmetric esters and of tBuOF as an electrophilic tert‐butoxylation agent is also mentioned. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Unique Epoxidationsmentioning

confidence: 99%

Section: Unique Epoxidationsmentioning

confidence: 99%

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Rozen

2005

Eur J Org Chem

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“…[1][2][3][4] Among various types of oxidation reactions, the oxidation of sulfides into sulfoxides (sulfoxidation) is of great importancei no rganic synthesis, [5] because sulfoxides are important intermediates or building blocks in the construction of pharmaceuticals, agrochemicals, and other valuable fine chemicals. [7][8][9][10][11] However,t hese methodss uffer from several drawbacks, such as low selectivity,t he high input of energy, and the release of highly toxic waste. [6] Therefore, interest in the selectiveo xidationo fs ulfides into sulfoxides has attracted great interest for al ong time.…”

Section: Introductionmentioning

confidence: 99%

“…Traditionally,t he oxidation of sulfides into sulfoxides has mainly been performed throught hermalo xidation processes by the use of severalk inds of oxidants, such as trifluoroperacetic acid, hydrogen peroxide, tert-butyl hydroperoxide, and iodobenzene diacetate. [7][8][9][10][11] However,t hese methodss uffer from several drawbacks, such as low selectivity,t he high input of energy, and the release of highly toxic waste. Therefore, the searchf or new routes for the efficient andenvironmentally friendly oxida-tion of sulfidesi nto sulfoxides has continued to be of interest in chemical research.…”

Section: Introductionmentioning

confidence: 99%

Metal‐ and Additive‐Free Oxidation of Sulfides into Sulfoxides by Fullerene‐Modified Carbon Nitride with Visible‐Light Illumination

et al. 2018

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Photocatalytic selective oxidation has attracted considerable attention as an environmentally friendly strategy for organic transformations. Some methods have been reported for the photocatalytic oxidation of sulfides into sulfoxides in recent years. However, the practical application of these processes is undermined by several challenges, such as low selectivity, sluggish reaction rates, the requirement of UV-light irradiation, the use of additives, and the instability of the photocatalyst. Herein, a metal-free C /graphitic carbon nitride (g-C N ) composite photocatalyst was fabricated by a facile method, and well characterized by TEM, SEM, FTIR spectroscopy, XRD, X-ray photoelectron spectroscopy, diffuse reflectance spectroscopy, and photoluminescence spectroscopy. The C /g-C N catalyst exhibited a high photocatalytic activity at room temperature for the selective oxidation of sulfides into the corresponding sulfoxides in the presence of other functional groups, due to the synergetic roles of C and g-C N . Several important parameters have been screened, and this method afforded good to excellent yields of sulfoxides under optimal conditions. The superoxide radical ( O ) and singlet oxygen ( O ) were identified as the oxidative species for the oxidation of sulfides into sulfoxides by exploring EPR experiments, and hence, a plausible mechanism for this oxidation was proposed. Moreover, the C /g-C N catalyst can be easily recovered by filtration and then reused at least four times without loss in activity.

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“…The conventional methods of carrying out this transformation include oxidation of the sulfide with peracids (i.e; m-CPBA or H 2 O 2 /acetic acid), or oxone [8]. Hydrogen peroxide with a variety of metal catalyst [9] as well as KMnO 4 [10] and Zn(MnO 4 ) 2 [11] have been used for this purpose. However, most of the existing methods are deficient in some respect such as: low yields, use expensive, toxic or rare oxidizing reagents, severe reaction conditions or difficulties with isolation of the product.…”

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confidence: 99%

An Efficient Method for the Oxidation of Organic Sulfides to Sulfones

Balicki

1999

J. prakt. Chem.

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Sulfones are useful intermediates which play an important role in organic chemistry [1]. These compounds are almost invariably prepared by oxidation of the corresponding organic sulfides [2][3][4][5][6][7]. The conventional methods of carrying out this transformation include oxidation of the sulfide with peracids (i.e; m-CPBA or H 2 O 2 /acetic acid), or oxone [8]. Hydrogen peroxide with a variety of metal catalyst [9] as well as KMnO 4 [10] and Zn(MnO 4 ) 2 [11] have been used for this purpose. However, most of the existing methods are deficient in some respect such as: low yields, use expensive, toxic or rare oxidizing reagents, severe reaction conditions or difficulties with isolation of the product. Oxidation of sulfides bearing bulky groups or electron withdrawing substituents is also often not satisfactory. Therefore, there is a need for simple, less expensive and safer methods for conversion of sulfides to sulfones. An Efficient Method for the Oxidation of Organic Sulfides to SulfonesRoman Balicki* Warszawa (Poland), Pharmaceutical Research Institute Received July 7th, 1998, respectively December 7th, 1998Keywords: Oxygenations, Reagents, Sulfur, Synthetic methods, Sulfones Abstract. Mild and safe oxidation of dialkyl-, diaryl-and alkyl-aryl sulfides (1a-m) to the corresponding sulfones (2a-A survey of the literature revealed that the adduct between hydrogen peroxide and urea (UHP) [12] is a cheap, safe and stable source of pure H 2 O 2 . Several systems containing UHP with some acid anhydrides were used as efficient oxidizing agents [13,14]. Recently, we reported that performic acid obtained by the combination of UHP and 85% formic acid appeared to be an effective reagent for mild and selective Noxidation of N-heteroaromatics and tertiary amines [15]. These results prompted us to extend the investigation of oxidizing abilities of this novel reagent.In this paper we wish to report on the facile and efficient oxidation of organic sulfides 1 to the respective sulfones 2 by use 85% HCOOH/UHP system. The reaction is very easy and proceeds within 1-4 hrs upon addition of the substrate 1 to a suspension of UHP in formic acid at room temperature to afford the corresponding sulfone 2, which precipitates during m)by using urea-hydrogen peroxide/formic acid system is reported.

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Oxidation of organic compounds by zinc permanganate

Cited by 74 publications

References 1 publication

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Metal‐ and Additive‐Free Oxidation of Sulfides into Sulfoxides by Fullerene‐Modified Carbon Nitride with Visible‐Light Illumination

An Efficient Method for the Oxidation of Organic Sulfides to Sulfones

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Oxidation of organic compounds by zinc permanganate

Cited by 74 publications

References 1 publication

Elemental Fluorine and HOF·CH3CN in Service of General Organic Chemistry

Elemental Fluorine and HOF·CH3CN in Service of General Organic Chemistry

Metal‐ and Additive‐Free Oxidation of Sulfides into Sulfoxides by Fullerene‐Modified Carbon Nitride with Visible‐Light Illumination

An Efficient Method for the Oxidation of Organic Sulfides to Sulfones

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Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry