Recent Advances in the Synthesis of Sulfoxides From Sulfides

Mata, Ernesto G.

doi:10.1080/10426509608038790

Cited by 82 publications

(35 citation statements)

References 230 publications

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“…They are also useful heteroatom functional groups in organic synthesis. For example, by oxidation of thioethers, chiral sulfoxides can be generated which can be used as auxiliaries in asymmetric synthesis [82][83][84][85]. Moreover, sulfones have been employed for stabilizing -radicals [86], -anions [87], can act as cationic synthons [88], and also for the formation of C-C bonds [89].…”

Section: S-alkylation Of Thiols With Alcoholsmentioning

confidence: 99%

Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis

Firouzabadi

Jafarpour

2008

JICS

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Both ZrCl 4 and ZrOCl 2 .8H 2 O are commercially available solid chemicals. Due to their low toxicities (LD 50 [ZrCl 4 oral rate] = 1688 mg/kg), (LD 50 [ZrOCl 2 .8H 2 O oral rate] = 2950 mg/kg), low costs, ease of handling, high activity, the zirconium(IV) compounds are potential green catalysts or reagents which are of importance from different views. In this review we have paid attention to the applications of these compounds as reagents or catalysts in Friedel-Crafts reactions, Fries rearrangements, reduction and oxidation reactions, cycloaddition and hydrometalation reactions, protection and deprotection of functional groups, reactions of epoxides, iodination of alcohols, S-alkylation of thiols with alcohols, Michael addition, condensation of indoles with carbonyl compounds, Claisen ester condensation, Baylis-Hillman reaction, preparation of organozirconium compounds and some other miscellaneous reactions.

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Section: S-alkylation Of Thiols With Alcoholsmentioning

confidence: 99%

Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis

Firouzabadi

Jafarpour

2008

JICS

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“…Synthesis of sulfoxides by the oxidation of thioethers has been extensively studied, which is illustrated by the fact that the results have been compiled and discussed in sevearal review articles. [35][36][37] The relation between thioethers and dioxiranes is quite old. The peroxide content of the acetone solution of the isolated dimethyldioxirane was determined by the oxidation of methyl phenyl sulfide (thioanisole) to its sulfoxide which was quantified either by GLC 38,39 or by 1 H-NMR spectroscopy.…”

Section: Oxidation Of Thioethers and Thiol Estersmentioning

confidence: 99%

Dioxirane oxidation of sulfur-containing organic compounds

Lévai¹

2003

Arkivoc

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Dedicated to Professor Branko AbstractThis short review describes the utilization of dioxiranes as convenient and extremely efficient electrophilic oxidants for the selective oxidation of sulfur-containing organic compounds. Relevant examples are included to illustrate the chemoselective and stereoselective oxidations of substances with several sites of oxidation. Electrophilic character of the dioxiranes is shown via the oxidation of compounds with two sulfur heteroatoms.

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“…Thus, even though the enantioselectivities are less spectacular than those achieved with isolated enzymes, for use on a preparative scale, this way of producing chiral sulfoxides is more convenient. To date, biological oxidation of sulfides to sulfoxides by means of whole cells has employed mainly fungi and bacteria and, to a lesser extent, yeasts [11][12][13].…”

Section: E-mail Address: Isidrogonzalez@ucaes (Ig Collado)mentioning

confidence: 99%

Enantiomeric oxidation of organic sulfides by the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride

Pinedo-Rivilla

Aleu

Collado

2007

Journal of Molecular Catalysis B: Enzymatic

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The biotransformations of a series of substituted sulfides were carried out with the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride. Several products underwent microbial oxidation of sulfide to sulfoxide with medium to high enantiomeric purity. With regard to sulfoxide enantioselectivity, the (R)-enantiomer was favoured in biotransformations by T. viride and E. lata while the (S)-enantiomer was favoured in those by B. cinerea. A minor amount of sulfone product was also obtained.

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Recent Advances in the Synthesis of Sulfoxides From Sulfides

Cited by 82 publications

References 230 publications

Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis

Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis

Dioxirane oxidation of sulfur-containing organic compounds

Enantiomeric oxidation of organic sulfides by the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride

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