On September 7, 2020, Kraszewski, Karol; Tomczyk, Ireneusz; Drabinska, Aneta; Bienkowski, Krzysztof; Solarska, Renata; Kalek, Marcin published an article.Name: 2,4-Di-tert-butylphenol The title of the article was Mechanism of Iodine(III)-Promoted Oxidative Dearomatizing Hydroxylation of Phenols: Evidence for a Radical-Chain Pathway. And the article contained the following:
The oxidative dearomatization of phenols with the addition of nucleophiles to the aromatic ring induced by hypervalent iodine(III) reagents and catalysts has emerged as a highly useful synthetic approach. However, exptl. mechanistic studies of this important process have been extremely scarce. In this report, we describe systematic investigations of the dearomatizing hydroxylation of phenols using an array of exptl. techniques. Kinetics, EPR spectroscopy, and reactions with radical probes demonstrate that the transformation proceeds by a radical-chain mechanism, with a phenoxyl radical being the key chain-carrying intermediate. Moreover, UV and NMR spectroscopy, high-resolution mass spectrometry, and cyclic voltammetry show that before reacting with the phenoxyl radical, the water mol. becomes activated by the interaction with the iodine(III) center, causing the Umpolung of this formally nucleophilic substrate. The radical-chain mechanism allows the rationalization of all existing observations regarding the iodine(III)-promoted oxidative dearomatization of phenols. The experimental process involved the reaction of 2,4-Di-tert-butylphenol(cas: 96-76-4).Name: 2,4-Di-tert-butylphenol
The Article related to phenol iodine oxidative dearomatization kinetics mechanism, hypervalent iodine, mechanistic investigations, phenol dearomatization, radical-chain pathway, synthetic methods and other aspects.Name: 2,4-Di-tert-butylphenol
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