Issue 37, 2018

Experimental evidence for the formation of cationic intermediates during iodine(iii)-mediated oxidative dearomatization of phenols

Abstract

Iodine(III)-based oxidants are commonly used reagents for the oxidative dearomatization of phenols. Having a better understanding of the mechanism through which these reactions proceed is important for designing new iodine(III)-based reagents, catalysts, and reactions. We have performed a Hammett analysis of the oxidative dearomatization of substituted 4-phenylphenols. This study confirms that iodine(III)-mediated oxidative dearomatizations likely proceed through cationic phenoxenium ions and not the direct addition of a nucleophile to an iodine-bound phenol intermediate.

Graphical abstract: Experimental evidence for the formation of cationic intermediates during iodine(iii)-mediated oxidative dearomatization of phenols

Supplementary files

Article information

Article type
Communication
Submitted
12 Jul 2018
Accepted
31 Ago 2018
First published
01 Sep 2018

Org. Biomol. Chem., 2018,16, 8249-8252

Author version available

Experimental evidence for the formation of cationic intermediates during iodine(III)-mediated oxidative dearomatization of phenols

T. Tang and A. M. Harned, Org. Biomol. Chem., 2018, 16, 8249 DOI: 10.1039/C8OB01652F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements