On the mechanism of the Elbs peroxydisulfate oxidation and a new peroxide rearrangement
Behrman, Elizabeth C. Chen, Ssuhen Behrman, Edward J.
Behrman, Elizabeth C.
Chen, Ssuhen
Behrman, Edward J.
Citations
Altmetric:
Other Names
Location
Time Period
Advisors
Original Date
Digitization Date
Issue Date
2002-04-22
Type
Article
Genre
Keywords
Caro's acid,Elbs oxidation,Peroxide,Phenol,Rearrangement
Subjects (LCSH)
Citation
Elizabeth C. Behrman, Ssuhen Chen, Edward J. Behrman, On the mechanism of the Elbs peroxydisulfate oxidation and a new peroxide rearrangement,Tetrahedron Letters, Volume 43, Issue 17, 2002, Pages 3221-3224,ISSN 0040-4039, https://doi.org/10.1016/S0040-4039(02)00495-1.
Abstract
Semiempirical calculations show that the intermediate formed by reaction between peroxydisulfate anion and the phenolate ion (the Elbs oxidation) is the species resulting from reaction of the tautomeric carbanion rather than the one resulting from attack by the oxyanion. This is confirmed by synthesis of the latter intermediate by reaction between Caro's acid dianion (peroxymonosulfate) and some nitro-substituted fluorobenzenes. This intermediate rearranges preferentially to give the phenol ortho-sulfate rather than the para-sulfate characteristic of the Elbs oxidation. This reaction of an arylperoxysulfate to give a phenol ortho-sulfate is a new rearrangement. © 2002 Elsevier Science Ltd. All rights reserved.
Table of Contents
Description
Click on the DOI link to access this article at the publisher's website (may not be free).
Publisher
Elsevier
Journal
Tetrahedron Letters
Book Title
Series
Digital Collection
Finding Aid URL
Use and Reproduction
Archival Collection
PubMed ID
ISSN
00404039