Isomerization of triphenylmethoxyl and 1,1-diphenylethoxyl radicals. Revised assignment of the electron-spin resonance spectra of purported intermediates formed during the ceric ammonium nitrate mediated photooxidation of aryl carbinols

DOI	Trouver le DOI : https://doi.org/10.1021/jo061898z
Auteur	Rechercher : Ingold, K. U.¹; Rechercher : Smeu, Manuel²; Rechercher : DiLabio, Gino A.²
Affiliation	Conseil national de recherches Canada. Institut Steacie des sciences moléculaires du CNRC Conseil national de recherches Canada. Institut national de nanotechnologie
Format	Texte, Article
Résumé	Grossi and Strazzari have reported (J. Org. Chem. 2000, 65, 2748−2754) that the ceric ammonium nitrate modulated photooxidation of triphenylmethanol and 1,1-diphenylethanol yielded ESR spectra of the putative spiro-cyclohexadienyl intermediates in the O-neophyl rearrangements of the corresponding alkoxyl radicals, Ph₂(R)CO• (R = Ph, CH₃), to the phenoxymethyl radicals, Ph(R)C•OPh. Both ESR spectra are reassigned to the phenoxyl radical, C₆H₅O•, and the probable mechanism by which phenoxyl is formed in these systems is presented.
Date de publication	2006-12-01
Dans	Journal Of Organic Chemistry 71, nº 26 (1 décembre 2006) : 9906–9908.
Langue	anglais
Numéro NPARC	12328225
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Identificateur de l’enregistrement	a066e80c-3b46-4d0d-83db-a17efd7d09c0
Enregistrement créé	2009-09-10
Enregistrement modifié	2020-04-22