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Isomerization of Triphenylmethoxyl: The Wieland Free‐Radical Rearrangement Revisited a Century Later
Author(s) -
DiLabio Gino A.,
Ingold K. U.,
Lin Shuqiong,
Litwinienko Grzegorz,
Mozenson Olga,
Mulder Peter,
Tidwell Thomas T.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201001008
Subject(s) - isomerization , content (measure theory) , constant (computer programming) , reaction rate constant , computer science , scheme (mathematics) , chemistry , photochemistry , philosophy , organic chemistry , mathematics , physics , kinetics , quantum mechanics , catalysis , mathematical analysis , programming language
Old wisdom teaches a new lesson : The rate constant for the isomerization of thermally generated triphenylmethoxyl to Ph 2 (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.