Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant

Kupwade, Ravindra V.; Khot, Sagar S.; Lad, Uday P.; Desai, Uday V.; Wadgaonkar, Prakash P.

doi:10.1007/s11164-017-3026-0

Cited by 28 publications

(16 citation statements)

References 59 publications

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“…Following the principles of 'green chemisty' a new environmentally friendly method for the sulfide oxidation at the ambient temperature by H 2 O 2 /H 2 O (oxidant/solvent) mixture was documented with high yields and non-toxicity of the corresponding (by-)products [35]. In 2017 an eco-friendly and catalyst-free method for oxidation of sulfides to sulfones, using Oxone (a stable 2:1:1 ternary composite of KHSO 5 , K 2 SO 4 and KHSO 4 ) was provided by Kupwade et al [36]. The previously available protocols in the chemoselective sulfides→sulfoxides oxidation by Oxone suffered from the drawbacks of thermal activation; therefore the energy-efficient combination of Oxone-KBr was proposed as an oxidant.…”

Section: Synthesis and Manufacturingmentioning

confidence: 99%

Sulfolane: Magic Extractor or Bad Actor? Pilot-Scale Study on Solvent Corrosion Potential

et al. 2018

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The sulfur-containing derivatives and their metabolites, regarded as ‘old devils of green’ chemistry, constitute a relevant class of air/water/soil contaminants in over-polluted world. In fact, some industrially-engineered solvents have become environmentally unfavorable. An attractive alternative to commonly used industrial liquids is sulfolane (C4H8SO2), an anthropogenic medium. The main objective of this paper is the comprehensive review focusing mainly on the state-of-the-art aspects of the sulfolane synthesis, application of sulfolane as an extractive solvent due to its ‘unique’ physicochemical properties as well as the potential of sulfolane to cause equipment corrosion and subsequent spills. The potential risk for groundwater contamination, danger for human health and ways of sulfolane biodegradation were briefly reviewed as well. Interestingly, the analysis performed on data stored in the Reaxys database revealed an alternating tendency of waxing and waning interest in sulfolane during the space of the last fifty years. Moreover, the primary goal of the presented case study was to verify applicability of industrial, multi-electrochemical technique for reliable detection of corrosion in low conductive process fluids. Several aspects of corrosion measurement including the impact of process parameters (temperature) and impurities (oxygen and chlorides) on stainless steel corrosion in pure sulfolane were investigated briefly.

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Section: Synthesis and Manufacturingmentioning

confidence: 99%

Sulfolane: Magic Extractor or Bad Actor? Pilot-Scale Study on Solvent Corrosion Potential

et al. 2018

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“…Regarding its use in the synthesis of organochalcogen compounds, Oxone® was used in the oxidation of sulfides to sulfoxides and sulfones, oxidation of thiols to sulfonic acids, oxyhalogenation of thiols and disulfides, oxidative coupling of thiols to disulfides, oxidation of selenides to selenones, and in the enantioselective oxidation of disulfides . Oxone® was used to prepare symmetric thiosulfonates, 3‐arylthio indoles, and 2‐aminobenzothiazoles …”

Section: Introductionmentioning

confidence: 99%

Selenomethoxylation of Alkenes Promoted by Oxone®

et al. 2018

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We describe herein an alternative method for the selenomethoxylation of unactivated alkenes using Oxone® as a stoichiometric oxidant. The electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone®. By this efficient and simple approach, β‐methoxy‐selenides were obtained in moderate to excellent yields at room temperature in an open flask, starting from alkenes by using methanol as both nucleophile and solvent. When a mixture of H2O/CH3CN was employed as the solvent, β‐hydroxy‐selenides were selectively obtained under mild conditions.

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“…It is well known that, oxone is a stable 2:1:1 ternary composite of KHSO5, K2SO4 and KHSO4 and it's use in various organic transformations is well documented. We have reported earlier the use of oxone in the oxidation of sulfides to sulfoxides as well as sulfones, 28 in the oxidation of hydrazides to diacylhydrazines. 29 However, the use of water being essential in oxone mediated oxidation of alcohols and the same being detrimental in the oxidation of α-hydroxyphosphonates, we focused our search on the reports on the use of water insoluble oxone derivatives in the oxidation of alcohols.…”

Section: Resultsmentioning

confidence: 99%

Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane

Kupwade¹,

Mitragotri²,

Kulkarni³

et al. 2021

Arkivoc

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Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant

Cited by 28 publications

References 59 publications

Sulfolane: Magic Extractor or Bad Actor? Pilot-Scale Study on Solvent Corrosion Potential

Sulfolane: Magic Extractor or Bad Actor? Pilot-Scale Study on Solvent Corrosion Potential

Selenomethoxylation of Alkenes Promoted by Oxone®

Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane

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