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<p>The photodegradation of a series of 4-hydroxy-4,9-dihydro-4<i>H</i>-xanthen-4-ones containing the photosensitive α-hydroxyketone fragment under UV irradiation (395 nm) was studied. The generation of hydroxyphenoxyl radicals (<i>a</i><sub>H</sub>(<i>C</i><sub>Ar</sub>−H) ≈ 2.00–2.40 G, <i>a</i><sub>H</sub>(Bu<sup>t</sup>) ≈ 0.30–0.35 G, <i>a</i><sub>H</sub>(CH<sub>2</sub>Ar) ≈ 0.75–0.85 G, <i>a</i><sub>H</sub>(OH) ≈ 0.4–0.5 G) was detected for all compounds by the ESR method. Under UV irradiation, hydroxyxanthenones undergo photoisomerization to form spirocyclohexadienones. Two derivatives of spiroketones were quantitatively isolated in the individual state after the irradiation (λ = 395 nm) of solutions of 1,3,5,7-tetrabutyl-4a-hydroxy-9<i>H</i>-xanthen-4(4a<i>H</i>)-one and 9,11-di-<i>tert</i>-butyl-7a-hydroxy-12<i>H</i>-benzo[<i>a</i>]xanthen-8(7a<i>H</i>)-one in chloroform.</p>

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Photodegradation of 4-hydroxy-4,9-dihydro-4H-xanthen-4-ones under UV irradiation

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • A. E. Tarakanova,
  • K. A. Kozhanov,
  • E. V. Baranov,
  • M. V. Arsenyev,
  • S. A. Chesnokov

摘要

The photodegradation of a series of 4-hydroxy-4,9-dihydro-4H-xanthen-4-ones containing the photosensitive α-hydroxyketone fragment under UV irradiation (395 nm) was studied. The generation of hydroxyphenoxyl radicals (aH(CAr−H) ≈ 2.00–2.40 G, aH(But) ≈ 0.30–0.35 G, aH(CH2Ar) ≈ 0.75–0.85 G, aH(OH) ≈ 0.4–0.5 G) was detected for all compounds by the ESR method. Under UV irradiation, hydroxyxanthenones undergo photoisomerization to form spirocyclohexadienones. Two derivatives of spiroketones were quantitatively isolated in the individual state after the irradiation (λ = 395 nm) of solutions of 1,3,5,7-tetrabutyl-4a-hydroxy-9H-xanthen-4(4aH)-one and 9,11-di-tert-butyl-7a-hydroxy-12H-benzo[a]xanthen-8(7aH)-one in chloroform.