Bulletin of the Chemical Society of Japan p. 199 - 207 (1998)
Update date:2022-08-03
Topics:
Goyal, Rajendra N.
Singhai, Naveen K.
The electrochemical oxidation of 1,3-dimethylxanthine has been studied in the pH range 2.3 - 10.3 at a pyrolytic graphite electrode. The conjugate base has been found as the electroactive species oxidized over the entire pH range. The 4e, 4H+ charge transfer step is followed by competitive irreversible chemical reactions. The decomposition of UV-absorbing intermediate generated during the electrooxidation has been found to follow first-order kinetics. The products of the EC reaction have been separated by HPLC and gel-permeation chromatography and characterized by mp, 1HNMR, and mass spectra. The presence of methyl groups of positions 1 and 3 has been found to affect the course of mechanism, because the positive charge developed on nitrogen does not permit ring contraction. A tentative mechanism has also been suggested.
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