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Photochemical Oxygenation of Phenols by Pyrimidopteridine N-Oxide. Comparative Studies with Pyridazine and Isoalloxazine N-Oxides

DOI: 10.1039/P19900003339

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 3339 - 3344 (1990)

Update date:2022-08-05

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Authors:

Sako, MagoichiSako, Magoichi

Ohara, SeijiOhara, Seiji

Hirota, KosakuHirota, Kosaku

Maki, YoshifumiMaki, Yoshifumi

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Article abstract of DOI:10.1039/P19900003339

1,3,7,9-Tetrabutylpyrimido<5,4-g>pteridine-2,4,6,8(1H,3H,7H,9H)-tetraone 5-oxide 1 transfers its N-oxide oxygen to phenols, i.e., phenol 5, p-cresol 6, L-tyrosine methyl ester 7, and p-hydroxyacetanilide (acetaminophen) 8, under photochemical conditions to give the corresponding dihydric phenols as major products without any accompanying photochemical intramolecular rearrangements of the N-oxide group taking place.This oxygenation is reasonably explained in terms of a photo-induced single electron transfer (SET) followed by oxygen-atom transfer (the SET mechanism) which occurs via the initial formation of a charge-transfer complex between compound 1 and the phenols employed.Comparative experiments with 3,10-dibutylisoalloxazine 5-oxide 3 and 3-methylpyridazine 2-oxide 4 well demonstrate the simplicity and the mechanistic characteristics of the photochemistry of compound 1.

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