Kraszewski, Karol; Tomczyk, Ireneusz; Drabinska, Aneta; Bienkowski, Krzysztof; Solarska, Renata; Kalek, Marcin published the artcile< Mechanism of Iodine(III)-Promoted Oxidative Dearomatizing Hydroxylation of Phenols: Evidence for a Radical-Chain Pathway>, Synthetic Route of 1530-33-2, the main research area is phenol iodine oxidative dearomatization kinetics mechanism; hypervalent iodine; mechanistic investigations; phenol dearomatization; radical-chain pathway; synthetic methods.
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.
Chemistry – A European Journal published new progress about Activation entropy. 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Synthetic Route of 1530-33-2.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary