Artículo
Sensitized photooxidation of Ortho-Prenyl Phenol: Biomimetic Dihydrobenzofuran Synthesis and Total 1O2 Quenching†
Fecha de publicación:
03/2023
Editorial:
Wiley Blackwell Publishing, Inc
Revista:
Photochemistry and Photobiology
ISSN:
0031-8655
e-ISSN:
1751-1097
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The sensitized photooxidation of ortho-prenyl phenol is described with evidence that solvent aproticity favors the formation of a dihydrobenzofuran [2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran], a moiety commonly found in natural products. Benzene solvent increased the total quenching rate constant (kT) of singlet oxygen with prenyl phenol by ~10-fold compared to methanol. A mechanism is proposed with preferential addition of singlet oxygen to prenyl site due to hydrogen bonding with the phenol OH group, which causes a divergence away from the singlet oxygen ‘ene’ reaction toward the dihydrobenzofuran as the major product. The reaction is a mixed photooxidized system since an epoxide arises by a type I sensitized photooxidation.
Palabras clave:
PRENYL PHENOL
,
PHOTOOXIDATION
,
NATURAL PRODUCTS
,
SINGLET OXYGEN
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Articulos (IDAS)
Articulos de INSTITUTO PARA EL DESARROLLO AGROINDUSTRIAL Y DE LA SALUD
Articulos de INSTITUTO PARA EL DESARROLLO AGROINDUSTRIAL Y DE LA SALUD
Citación
Jabeen, Shakeela; Ghosh, Goutam; Lapoot, Lloyd; Durantini, Andres Matías; Greer, Alexander; Sensitized photooxidation of Ortho-Prenyl Phenol: Biomimetic Dihydrobenzofuran Synthesis and Total 1O2 Quenching†; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 99; 2; 3-2023; 637-641
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