• In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to...
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  • pyridinium chlorochromate) or dimethyl sulfoxide (e.g. Swern oxidation) or Dess–Martin oxidation due to its use of relatively mild and non-toxic reagents...
    12 KB (1,250 words) - 17:28, 13 May 2022
  • Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters...
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  • Thumbnail for Dess–Martin periodinane
    Parikh–Doering oxidation Albright-Goldman oxidation Swern oxidation Corey–Kim oxidation Ley oxidation (TPAP oxidation) TEMPO oxidation Dess, D. B.; Martin, J. C. (1983)...
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  • chemist Choung Un Kim. Although the Corey–Kim oxidation possesses the distinctive advantage over Swern oxidation of allowing an operation above –25 °C, it...
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  • displaced by the Swern oxidation, which also uses DMSO as an oxidant in the presence of an electrophilic activator. Swern oxidations tend to give higher...
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  • Swern is a surname. Notable people with the surname include: Daniel Swern (1916–1982), American chemist Swern oxidation, an organic chemical reaction...
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  • Thumbnail for N,N-Diisopropylethylamine
    Although triethylamine is traditionally employed as the hindered base in Swern oxidations, the structurally similar DIPEA can be used instead, as exemplified...
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  • Thumbnail for Aldehyde
    pre-oxidized substrates: various sulfoxides (e.g. the Swern oxidation), or amine oxides (e.g., the Ganem oxidation). Sterically-hindered nitroxyls (i.e., TEMPO)...
    30 KB (3,092 words) - 21:58, 27 November 2024
  • synthetic route is shown below: Swern oxidation Pfitzner–Moffatt oxidation Corey–Kim oxidation Tidwell, Thomas T. (1990). "Oxidation of Alcohols to Carbonyl Compounds...
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  • Thumbnail for Phosphorus pentoxide
    of P4O10 in DMSO, is employed for the oxidation of alcohols. This reaction is reminiscent of the Swern oxidation. The desiccating power of P4O10 is strong...
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  • to the corresponding ketone). Selective oxidation of alcohols to aldehydes requires circumventing over-oxidation to the carboxylic acid. One popular approach...
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  • Thumbnail for Dimethyl sulfoxide
    sulfonium-based oxidation reactions including the Pfitzner–Moffatt oxidation, Corey–Kim oxidation and the Swern oxidation. The Kornblum oxidation is conceptually...
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  • Thumbnail for Oxalyl chloride
    the corresponding aldehydes and ketones via the process known as the Swern oxidation. Oxalyl chloride is mainly used together with a N,N-dimethylformamide...
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  • Thumbnail for Albright–Goldman oxidation
    the oxidation of primary alcohols to aldehydes is the Swern oxidation. J. Donald Albright, Leon Goldman (1965), "Indole Alkaloids. III.1 Oxidation of Secondary...
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  • Daniel Swern (January 21, 1916 – December 5, 1982) was an American chemist who discovered the Swern oxidation. "After deadline". Journal of the American...
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  • Thumbnail for 1-Propanol
    of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid. 1-Propanol is...
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  • Thumbnail for Thermal runaway
    they are very prone to hazardous thermal runaway. For example, in Swern oxidation, the formation of sulfonium chloride must be performed in a cooled...
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  • Thumbnail for Methanesulfonic anhydride
    monosaccharides, the acetylation was not completed. Like Pfitzner–Moffatt oxidation and Swern oxidation, with DMSO, Ms2O can oxidize primary and secondary alcohols...
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  • carbonyl groups Suzuki coupling Swain equation Swarts reaction Swern oxidation Tamao oxidation Tafel rearrangement Takai olefination Tebbe olefination ter...
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  • Thumbnail for Trifluoroacetic anhydride
    Pummerer rearrangement. It can be used in place of oxalyl chloride in the Swern oxidation, allowing temperatures up to −30 °C. With sodium iodide, it reduces...
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  • Thumbnail for Dimethyl sulfide
    ozonolysis of alkenes. It reduces the intermediate trioxolane. The Swern oxidation produces dimethyl sulfide by reduction of dimethylsulfoxide. With chlorinating...
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  • Thumbnail for Cyanuric chloride
    chloride can also be used as an alternative to oxalyl chloride in the Swern oxidation. Thiazyl chloride trimer – structural analogue with sulfur atoms in-place...
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  • stereocontrol because in the next step the alcohol is oxidized in a Swern oxidation to ketone 11. A Staudinger reaction with triphenylphosphine closes...
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  • Thumbnail for 2-Iodoxybenzoic acid
    β-hydroxyketones to β-diketones. IBX provides yields superior to both the Swern and Dess–Martin oxidation protocols. Boeckman, R. K. Jr.; Shao, P.; Mullins, J. J. (2000)...
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  • Thumbnail for N-tert-Butylbenzenesulfinimidoyl chloride
    final product, a Mannich base. Swern oxidation Pfitzner–Moffatt oxidation Corey–Kim oxidation Parikh–Doering oxidation Matsuo, J.; Mukaiyama, T. (2001)...
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  • Thumbnail for Oxoammonium-catalyzed oxidation
    partial oxidation is effected with TEMPO and hypochlorite, then chlorite is added to complete the oxidation. Only primary alcohol oxidation is observed...
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  • Thumbnail for Strychnine total synthesis
    allylic oxidation (Pd(OAc)2 / AcOH / benzoquinone / MnO2) to tetracycle 7. Hydroboration-oxidation (9-BBN / H2O2) gave alcohol 8 and subsequent Swern oxidation...
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  • Thumbnail for Dry ice
    195 K), which can be used for instance to prevent thermal runaway in a Swern oxidation. The process of altering cloud precipitation can be done with the use...
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  • epoxidation Oppenauer oxidation Prilezhaev reaction Rubottom oxidation Schmidt reaction Swern oxidation Wacker-Tsuji oxidation Reduction Birch reduction...
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