Experimental evidence for the formation of cationic intermediates during iodine(iii)-mediated oxidative dearomatization of phenols. Issue 37 (7th September 2018)

• Record Type: Journal Article
• Authors: Tang, Ting; Harned, Andrew M.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 37(2018)
• Page Start: 8249
• Page End: 8252
• Publication Date: 2018-09-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01652f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Hammett analysis reveals iodine(iii )-mediated oxidative dearomatization reactions proceed through cationic intermediates and not direct nucleophilic attack on an activated phenol. 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.