The oxidation of 2-alkoxy-3,6-di- tert-butylphenols. The reversible dimerization of 2-alkoxy-3,6-di- tert-butylphenoxy radicals

[Display omitted] The oxidation of 2-alkoxy-3,6-di- tert-butylphenols has been studied. It was found that 2-RO-3,6-di- tert-butylphenoxy radicals (R = Et, Pr, Ph) undergo dimerization by C–O coupling. The X-ray structure of 2-ethoxy-3,6-di- tert-butylphenoxy dimer has been determined. Radical dimers...

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Published inTetrahedron letters Vol. 46; no. 23; pp. 4095 - 4097
Main Authors Abakumov, Gleb A., Cherkasov, Vladimir K., Nevodchikov, Vladimir I., Druzhkov, Nikolai O., Fukin, Georgii K., Kursky, Yurii A., Piskunov, Alexandr V.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.06.2005
Elsevier
Subjects
Chemistry
Chemistry, Organic
Oxidation
Phenol
Phenoxy radical
Physical Sciences
Reversible dissociation
Science & Technology
Reversible dissociation
Phenol
Oxidation
Phenoxy radical
oxidation
phenol
reversible dissociation
phenoxy radical
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Summary:[Display omitted] The oxidation of 2-alkoxy-3,6-di- tert-butylphenols has been studied. It was found that 2-RO-3,6-di- tert-butylphenoxy radicals (R = Et, Pr, Ph) undergo dimerization by C–O coupling. The X-ray structure of 2-ethoxy-3,6-di- tert-butylphenoxy dimer has been determined. Radical dimers dissociate reversibly in solution to give two phenoxy radicals at 200–350 K. By using EPR spectroscopy the equilibrium concentration of the phenoxy radicals, equilibrium constants and Δ H and Δ S of dissociation have been determined.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.04.012