| Elbs persulfate oxidation | |
|---|---|
| Named after | Karl Elbs |
| Reaction type | Organic redox reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000179 |
The Elbs persulfate oxidation is the organic reaction of phenols with alkaline potassium persulfate to form para-diphenols.[1] The reaction is generally performed in water at room temperatures or below, using equimolar quantities of reagents.
Several reviews have been published.[2][3][4]
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Iodide Persulfate Kinetics
Transcription
Scope and mechanism
The reaction is disadvantaged by moderate to low chemical yields with recovery of starting material and complete consumption of the persulfate.[4] It is suggested that the phenol in many cases is a catalyst converting the persulfate into a sulfate. Despite this, the Elbs reaction remains generally useful in a research setting, as it is simple to perform and is tolerant of a wide range of other functional groups, which are not oxidised under these conditions.[4]
A reaction mechanism has been postulated which accounts for the observed para substitution featuring the tautomeric para carbanion of the starting phenolate ion:[5] It begins with nucleophilic displacement on the peroxide oxygen of the peroxodisulfate (peroxydisulfate) ion, to give an intermediate sulfate group (3), which is then hydrolyzed to the hydroxyl group.
See also
References
- ^ Elbs, K. (1893). "Ueber Nitrohydrochinon". J. Prakt. Chem. (in German). 48: 179–185. doi:10.1002/prac.18930480123.
- ^ Sethna, S. M. (1951). "The Elbs Persulfate Oxidation". Chem. Rev. 49 (1): 91–101. doi:10.1021/cr60152a002.
- ^ Lee, J. B.; Uff, B. C. (1967). "Organic reactions involving electrophilic oxygen". Quart. Rev. 21 (4): 453. doi:10.1039/qr9672100429.
- ^ a b c Behrman, E. J. (1988). "The Persulfate Oxidation of Phenols and Arylamines (The Elbs and the Boyland-Sims Oxidations)". Org. React. Vol. 35. pp. 421–511. doi:10.1002/0471264180.or035.02. ISBN 0471264180.
- ^ Behrman, E. J. (2006). "The Elbs and Boyland-Sims peroxydisulfate oxidations". Beilstein Journal of Organic Chemistry. 2 (1): 22. doi:10.1186/1860-5397-2-22. PMC 1697820. PMID 17090305.
Add the following: E. J. Behrman, The Elbs & Boyland-Sims Oxidations: An Updated Literature Survey. Mini-Rev. Org. Chem, 18(2021)621-625.
This page was last edited on 3 December 2023, at 10:08