Elbs persulfate oxidation
- Elbs persulfate oxidation
The Elbs persulfate oxidation is the organic reaction of phenols with alkaline potassium persulfate to form para-diphenols. [Elbs, K. "J. Prakt. Chem." 1893, "48", 179.]
Several review have been published. [cite journal | author = S. M. Sethna | title = The Elbs Persulfate Oxidation | year = 1951 | journal = Chem. Rev. | volume = 49 | issue = 1 | pages = 91–101 | doi = 10.1021/cr60152a002] [Lee, J. B.; Uff, B. C. "Quart. Rev." 1967, "21", 453. (Review)] [Behrman, E. J. "Org. React." 1988, "35", 421-511. (Review)]
Reaction mechanism
A reaction mechanism has been postulated accounting for the observed para substitution featuring the tautomeric para carbanion of the starting phenolate ion: [cite journal | author = E. J. Behrman | title = The Elbs and Boyland-Sims peroxydisulfate oxidations | year = 2006 | journal = Beilstein Journal of Organic Chemistry | volume = 2 | issue = 1 | pages = 22 | doi = 10.1186/1860-5397-2-22]
which gives a nucleophilic displacement on the peroxide oxygen of the peroxodisulfate (peroxydisulfate) ion. The intermediate sulfate group is then hydrolyzed to the alcohol.
The reaction is disadvantaged by low chemical yields with recovery of starting material and complete consumption of the persulfate. It is suggested that the phenol in many cases is a catalyst converting the persulfate into a sulfate.
References
ee also
* Boyland-Sims oxidation
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