Arene oxidation with malonoyl peroxides

Dragan, A., Kubczyk, T. M., Rowley, J. H., Sproules, S. and Tomkinson, N. C. O. (2015) Arene oxidation with malonoyl peroxides. Organic Letters, 17(11), pp. 2618-2621. (doi:10.1021/acs.orglett.5b00953) (PMID:25966313)

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Abstract

Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations and reactivity profile studies is proposed.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Sproules, Dr Stephen and Tomkinson, Dr Nicholas
Authors: Dragan, A., Kubczyk, T. M., Rowley, J. H., Sproules, S., and Tomkinson, N. C. O.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Copyright Holders:Copyright © 2015 American Chemical Society
First Published:First published in Organic Letters 17(11):2618-2621
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher.

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