Mono-, di-, and tri prenyl phloroglucinol derivatives were synthesized and their reactions with singlet oxygen (1O2) were studied. 2-(3-Methylbut-2-en-1-yl)benzene-1,3,5-triol, 5-hydroxy-2,2-bis(3-methybut-2-enyl)cyclohex-4-ene-1,3-dione, and 5-hydroxy-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione underwent “ene” reactions with 1O2. The resulting hydroperoxides were characterized by 1H NMR spectroscopy, and their reductions to the corresponding alcohols with triphenylphosphine were studied. In these photooxidations, 1O2 was generated by the irradiation of molecular oxygen in the presence of rose bengal and silicon phthalocyanine dichloride as the photosensitizers in deuterated solvents such as CD3OD and CDCl3, respectively, at 25 °C.

Sensitized photooxidations of mono-, di-, and tri prenylated phloroglucinol derivatives

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.