The oxidation of alkyl sulphides

Edwards, David R.; Stenlake, J. B.

doi:10.1039/jr9540003272

Cited by 43 publications

(15 citation statements)

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“…46 Iodosobenzene diacetate caused diacetoxylation 59 of the heterocycle of 2,5-diphenyl-l,4-dithiadiene rather than oxidation of the sulfide function, and with 2,5-diphenyl-l,4-dithiadiene-l-oxide unexpected results were obtained, as discussed in section C-4. Manganese dioxide 50 gives good yields of dibutyl and dibenzyl sulfoxides, a poor yield of diallyl sulfoxide, and fails to oxidize bis(2,4-dinitrophenyl) sulfide. Manganese dioxide 50 gives good yields of dibutyl and dibenzyl sulfoxides, a poor yield of diallyl sulfoxide, and fails to oxidize bis(2,4-dinitrophenyl) sulfide.…”

Section: B Methods Of Preparation Of Sulfoxidesmentioning

confidence: 99%

Chemistry of the Sulfoxide Group

Szmant

1961

Organic Sulfur Compounds

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Section: B Methods Of Preparation Of Sulfoxidesmentioning

confidence: 99%

Chemistry of the Sulfoxide Group

Szmant

1961

Organic Sulfur Compounds

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“…However, due to the high tendency of sulfides to undergo over oxidation to sulfones, it is not conventionally used for the oxidation of sulfides. Chromic acid-pyridine combination has been demonstrated to be highly effective in chemoselective and controlled oxidation of sulfide to sulfoxides (Scheme 9) [62].…”

Section: Chromic Acidmentioning

confidence: 99%

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Kupwade

2019

J. Chem. Rev.

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A large variety of organosulfur compounds have been shown to having diverse biological effects such as antioxidant effects, anti-inflammatory properties, inhibition of platelet aggregation, reduction of systolic blood pressure, and reduction of cholesterol. Among these, sulfoxides and sulfones show wide and significant applications as commodity chemical in various fields of chemistry. Therefore, synthesis of sulfoxides as well as sulfones has remained a point of attraction for synthetic organic chemists. Among array of methods used to synthesize the sulfoxides or sulfones, oxidation of sulfide is the most convenient way. This review precises chemoselective methods for the synthesis of the sulfoxides as well as sulfones focusing on oxidative protocols. This review will aid researchers to explore and utilise the mentioned protocols for different organic transformations.

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“…In addition, sulfinic acids are inherently unstable, decomposing via over/underoxidation, elimination, and reactivity toward electrophiles. 19,20 Therefore, they are often synthesized freshly or generated in situ, further complicating synthetic pathways. These drawbacks have led to a focus on new methods to produce sulfinic acids for the preparation of sulfones, sulfonamides, and sulfonyl fluorides.…”

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confidence: 99%

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions

Day

Neill

et al. 2017

Org. Lett.

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Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.

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The oxidation of alkyl sulphides

Cited by 43 publications

References 0 publications

Chemistry of the Sulfoxide Group

Chemistry of the Sulfoxide Group

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions

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