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Die photosensibilisierte Oxydation einwertiger Phenole zu Chinonen
Author(s) -
Pfoertner K.,
Böse D.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530702
Subject(s) - chemistry , adduct , phenols , electrophile , phenol , solvent , radical , singlet oxygen , medicinal chemistry , photochemistry , oxygen , organic chemistry , catalysis
The photosensitized oxidation of methyl substituted phenols with free para ‐positions starts with an electrophilic attack of position 4 by singlet oxygen. This follows from the course of the reaction using phenols with methyl groups in different positions. The influence of the solvent shows that the hydroperoxide formation from the primary oxygen adduct proceeds via an inter ‐molecular hydrogen shift. The solvent is the hydrogen donator, whereas the phenoxy radicals resulting from the oxidation of the phenol by the excited sensitizer are the hydrogen acceptors. Finally, the quinones are formed from the hydroperoxides by elimination of water.