A. E. Tarakanova, K. A. Kozhanov, E. V. Baranov, M. V. Arsenyev, S. A. Chesnokov
{"title":"紫外光照射下4-羟基-4,9-二氢- 4h -杂原烯-4-酮的光降解","authors":"A. E. Tarakanova, K. A. Kozhanov, E. V. Baranov, M. V. Arsenyev, S. A. Chesnokov","doi":"10.1007/s11172-025-4589-3","DOIUrl":null,"url":null,"abstract":"<div><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></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"947 - 955"},"PeriodicalIF":1.7000,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photodegradation of 4-hydroxy-4,9-dihydro-4H-xanthen-4-ones under UV irradiation\",\"authors\":\"A. E. Tarakanova, K. A. Kozhanov, E. V. Baranov, M. V. Arsenyev, S. A. Chesnokov\",\"doi\":\"10.1007/s11172-025-4589-3\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><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></div>\",\"PeriodicalId\":756,\"journal\":{\"name\":\"Russian Chemical Bulletin\",\"volume\":\"74 4\",\"pages\":\"947 - 955\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2025-05-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Chemical Bulletin\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11172-025-4589-3\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-025-4589-3","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Photodegradation of 4-hydroxy-4,9-dihydro-4H-xanthen-4-ones under UV irradiation
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.
期刊介绍:
Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections:
General and Inorganic Chemistry;
Physical Chemistry;
Organic Chemistry;
Organometallic Chemistry;
Chemistry of Natural Compounds and Bioorganic Chemistry.