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Benzene solvent increased the total quenching rate constant (<jats:italic>k<\/jats:italic><jats:sub>T<\/jats:sub>) of singlet oxygen with prenyl phenol by ~10\u2010fold 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 \u2018ene\u2019 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.<\/jats:p>","DOI":"10.1111\/php.13689","type":"journal-article","created":{"date-parts":[[2022,8,18]],"date-time":"2022-08-18T00:23:00Z","timestamp":1660782180000},"page":"637-641","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Sensitized Photooxidation of <i>Ortho<\/i>\u2010Prenyl Phenol: Biomimetic Dihydrobenzofuran Synthesis and Total <scp><sup>1<\/sup>O<sub>2<\/sub><\/scp> Quenching<sup>\u2020<\/sup>"],"prefix":"10.1111","volume":"99","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7153-3379","authenticated-orcid":false,"given":"Shakeela","family":"Jabeen","sequence":"first","affiliation":[{"name":"Department of Chemistry Brooklyn College of the City University of New York  Brooklyn New York 11210 USA"},{"name":"Ph.D. Program in Chemistry The Graduate Center of the City University of New York 365 Fifth 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