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Medientyp: E-Artikel Titel: New Insights into the Reactivity of Nitrogen Dioxide with Substituted Phenols: A Solvent Effect Beteiligte: Astolfi, Paola; Panagiotaki, Maria; Greci, Lucedio Erschienen: Wiley, 2005 Erschienen in: European Journal of Organic Chemistry Sprache: Englisch DOI: 10.1002/ejoc.200500016 ISSN: 1434-193X; 1099-0690 Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry Entstehung: Anmerkungen: Beschreibung: <jats:title>Abstract</jats:title><jats:p>Various alkyl‐substituted phenols react readily with nitrogen dioxide (<jats:sup><jats:bold>·</jats:bold></jats:sup>NO<jats:sub>2</jats:sub>) in different solvents at room temperature. In all cases nitration is the major reaction and leads to the formation of mono‐ and dinitrophenols and 4‐nitrocyclohexa‐2,5‐dienones from 2,4,6‐tri‐substituted phenols. Oxidation, dimerisation and, in one case, nitrosation are also observed. The reaction pathway followed changes according to the solvent and to the nature and the number of substituents on the phenolic ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)</jats:p>