Isomerization of Triphenylmethoxyl: The Wieland Free-Radical Rearrangement Revisited a Century Later

Isomerization of Triphenylmethoxyl: The Wieland Free-Radical Rearrangement Revisited a Century Later

Old wisdom teaches a new lesson: The rate constant for the isomerization of thermally generated triphenylmethoxyl to Ph2(PhO)C. has been determined both experimentally and by DFT calculations (see scheme), and the results vindicated Wieland′s 1911 observations and conclusions—in contrast to photoche...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-08, Vol.49 (34), p.5982-5985
Hauptverfasser: DiLabio, Gino A, Ingold, K.U, Lin, Shuqiong, Litwinienko, Grzegorz, Mozenson, Olga, Mulder, Peter, Tidwell, Thomas T
Format: Artikel
Sprache:eng
Schlagworte:
peroxide
radical reactions
reaction kinetics
rearrangements
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Zusammenfassung:Old wisdom teaches a new lesson: The rate constant for the isomerization of thermally generated triphenylmethoxyl to Ph2(PhO)C. has been determined both experimentally and by DFT calculations (see scheme), and the results vindicated Wieland′s 1911 observations and conclusions—in contrast to photochemically based findings.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001008