Elsevier, Bioorganic and Medicinal Chemistry Letters, 4(11), p. 443-445
DOI: 10.1016/s0960-894x(00)00690-9
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Certain alkaloids were observed to undergo N-demethylation processes under photochemical conditions. Tropine, acetyltropine, tropinone, and atropine were cleanly N-demethylated upon treatment with tetraphenylporphin, oxygen, and light. Dextromethorphan also underwent a N-demethylation reaction, but reacted further to afford an imine. In contrast, 14-acyloxycodeinones underwent a photochemically induced tandem N-demethylation acyl migration.