Oxidation of sulfides to sulfoxides. Part 1: Oxidation using halogen derivatives

Kowalski, Piotr; Mitka, Katarzyna; Ossowska, Katarzyna; Kolarska, Zofia

doi:10.1016/j.tet.2004.11.041

Cited by 213 publications

(86 citation statements)

References 148 publications

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“…1, observed in the first 3 min of the reaction, were intermediate species. operative in the oxidation of organic sulfides with bromine, resulting in the corresponding sulfoxides [43,44]. Furthermore, the same reaction mechanism was suggested by Natile et al in the kinetic study of the reduction gold(III) to gold(I) by dialkyl sulfides in aqueous methanol solution [32].…”

Section: The Reactions Between Hmentioning

confidence: 72%

A spectroscopic and electrochemical investigation of the oxidation pathway of glycyl-d,l-methionine and its N-acetyl derivative induced by gold(III)

et al. 2011

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Section: The Reactions Between Hmentioning

confidence: 72%

A spectroscopic and electrochemical investigation of the oxidation pathway of glycyl-d,l-methionine and its N-acetyl derivative induced by gold(III)

et al. 2011

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Section: Sulfides To Sulfoxidesmentioning

confidence: 99%

“…Historically, sulfur-containing compounds have figured as targets for their importance to the pharmaceutical industry as antibacterial agents [25]. Therefore, the development of catalytic systems for the preparation of optically active sulfoxides is important, because they are chiral synthons [50] in the synthesis of bioactive compounds [51]. Sulfoxidation is commonly presented as being a direct pathway for generating sulfoxides, however, most of the reagents used for this reaction such as iodosylbenzene, peroxyacids, and stoichiometric oxo-metal oxidants are unsatisfactory due to their high toxicity and low chemoselectivity between sulfoxide and sulfone products [52].…”

Section: Sulfides To Sulfoxidesmentioning

confidence: 99%

Porphyrins as Catalysts in Scalable Organic Reactions

et al. 2016

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Catalysis is a topic of continuous interest since it was discovered in chemistry centuries ago. Aiming at the advance of reactions for efficient processes, a number of approaches have been developed over the last 180 years, and more recently, porphyrins occupy an important role in this field. Porphyrins and metalloporphyrins are fascinating compounds which are involved in a number of synthetic transformations of great interest for industry and academy. The aim of this review is to cover the most recent progress in reactions catalysed by porphyrins in scalable procedures, thus presenting the state of the art in reactions of epoxidation, sulfoxidation, oxidation of alcohols to carbonyl compounds and C-H functionalization. In addition, the use of porphyrins as photocatalysts in continuous flow processes is covered.

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“…Chlorination and oxidation done with the help of N-Chlorosuccinamide is significant which makes it a versatile reagent [7]. It carries as oxidizing agent in both acidic and alkaline media [5,6,[8][9][10][11][12][13][14][15][16] [11,13,14].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Study on Kinetics of Oxidation of Doxycycline Hydrochloride by N-Chlorosuccinamide in Acidic Medium

Shastry¹,

Asha²,

Sateesh³

2017

Asian J. Chem.

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A tetracycline antibiotic doxycycline hydrochloride (DOX) has been oxidized by N-chlorosuccinamide (NCS) in sulphuric acid medium at 303 K and the kinetics have been investigated. The stoichiometry of the reaction was found to be 1:1 where one mole doxycycline reacted with one mole of NCS and the product of oxidation of doxycycline, 1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,4,11-trioxotetracene-2-carboxamide is identified by the spot tests and confirmed by LC-MS spectral analysis. The titled reaction exhibited first-order kinetics with reference to concentration of NCS and doxycycline a fractional order kinetics was observed with respect to [H2SO4] and doxycycline. The changes in the reaction rate on the addition of halide ions and reduction product was studied. The influence of added product, p-toluene sulfonamide was studied and found no significant effect. The influence of ionic strength (NaClO4) and dielectric constant of the medium was investigated on the reaction rate. All the experimental values were compiled together and a mechanism was proposed. The temperature effect was studied for calculating the activation parameters with reference to the rate determining step in the mechanism and the thermodynamic parameters were also discussed.

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Oxidation of sulfides to sulfoxides. Part 1: Oxidation using halogen derivatives

Cited by 213 publications

References 148 publications

A spectroscopic and electrochemical investigation of the oxidation pathway of glycyl-d,l-methionine and its N-acetyl derivative induced by gold(III)

A spectroscopic and electrochemical investigation of the oxidation pathway of glycyl-d,l-methionine and its N-acetyl derivative induced by gold(III)

Porphyrins as Catalysts in Scalable Organic Reactions

Spectroscopic Study on Kinetics of Oxidation of Doxycycline Hydrochloride by N-Chlorosuccinamide in Acidic Medium

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