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Oxidative Cleavage of Pyrocatechol at the meta ‐Position; A Model Reaction for Cleavage by Pyrocatechol‐2,3‐dioxygenase?
Author(s) -
Müller Rudolf,
Lingens Franz
Publication year - 1984
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198400791
Subject(s) - oxidative cleavage , chemistry , cleavage (geology) , picolinic acid , sulfoxide , dioxygenase , oxidative phosphorylation , dimethyl sulfoxide , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , enzyme , materials science , fracture (geology) , composite material
The first nonenzymatic meta ‐cleavage of pyrocatechol 1 was achieved with KO 2 in dimethyl sulfoxide. The unstable yellow 2‐hydroxymuconaldehyde acid 2 was converted into picolinic acid. Since 1 is not cleaved to give 2 under N 2 , O 2 ⊖as well as O 2 might participate in the reaction.