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| Natura: | Artículo Open Access |
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Wiley
2025
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| Accesso online: | https://onlinelibrary.wiley.com/doi/10.1111/php.70005 |
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| _version_ | 1867012995102539776 |
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| author | Kamrun Nahar Serah Essang Lloyd Lapoot Alexander Greer |
| author_facet | Kamrun Nahar Serah Essang Lloyd Lapoot Alexander Greer Kamrun Nahar Serah Essang Lloyd Lapoot Alexander Greer |
| collection | Wiley Open Access |
| contents | Tandem singlet oxygenation: Regioselective reaction of two 1 O 2 molecules by a nonconjugated diprenyl phenol Kamrun Nahar Serah Essang Lloyd Lapoot Alexander Greer Photochemistry and Photobiology Abstract Tandem reactions of singlet oxygen ( 1 O 2 ) with nonconjugated natural products, such as plastoquinones, have attracted attention. However, mechanistic clarity is needed for the 1 O 2 uptake sequence and regioselectivity. Our strategy was to study a tandem 1 O 2 reaction in a diprenylated phenol (geranyl phenol) bearing an inner and an outer prenyl group in the chain. Singlet oxygen first added to the inner prenyl group by H‐bonding to the phenol OH, forming a gem ‐disubstituted and a tri ‐substituted dienyl dihydrobenzofuran. H 2 O 2 was also released as a by‐product. A second equivalent of 1 O 2 added by an “ene” reaction, but now to the outer rather than the inner site of the nonconjugated diene to reach four hydroperoxy‐dihydrobenzofurans. There was no evidence for 1 O 2 “ene” reactions on the inner prenyl sites, but product decomposition included the formation of oxygen‐centered radicals and even methane by a β‐scission process. The results are an essential step in resolving mechanistic puzzles of reactive oxygen uptake in natural prenylated systems, which are important topics not only in physical‐organic and synthetic chemistry but also in plant oxidation chemistry. 10.1111/php.70005 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| doi_str_mv | 10.1111/php.70005 |
| format | Artículo Open Access |
| id | wiley_oa_10_1111_php_70005 |
| institution | Wiley Open Access |
| license_str_mv | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| publishDate | 2025 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Tandem singlet oxygenation: Regioselective reaction of two 1 O 2 molecules by a nonconjugated diprenyl phenol Kamrun Nahar Serah Essang Lloyd Lapoot Alexander Greer Photochemistry and Photobiology Tandem singlet oxygenation: Regioselective reaction of two 1 O 2 molecules by a nonconjugated diprenyl phenol Kamrun Nahar Serah Essang Lloyd Lapoot Alexander Greer Photochemistry and Photobiology Abstract Tandem reactions of singlet oxygen ( 1 O 2 ) with nonconjugated natural products, such as plastoquinones, have attracted attention. However, mechanistic clarity is needed for the 1 O 2 uptake sequence and regioselectivity. Our strategy was to study a tandem 1 O 2 reaction in a diprenylated phenol (geranyl phenol) bearing an inner and an outer prenyl group in the chain. Singlet oxygen first added to the inner prenyl group by H‐bonding to the phenol OH, forming a gem ‐disubstituted and a tri ‐substituted dienyl dihydrobenzofuran. H 2 O 2 was also released as a by‐product. A second equivalent of 1 O 2 added by an “ene” reaction, but now to the outer rather than the inner site of the nonconjugated diene to reach four hydroperoxy‐dihydrobenzofurans. There was no evidence for 1 O 2 “ene” reactions on the inner prenyl sites, but product decomposition included the formation of oxygen‐centered radicals and even methane by a β‐scission process. The results are an essential step in resolving mechanistic puzzles of reactive oxygen uptake in natural prenylated systems, which are important topics not only in physical‐organic and synthetic chemistry but also in plant oxidation chemistry. 10.1111/php.70005 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| title | Tandem singlet oxygenation: Regioselective reaction of two 1 O 2 molecules by a nonconjugated diprenyl phenol |
| topic | Photochemistry and Photobiology |
| url | https://onlinelibrary.wiley.com/doi/10.1111/php.70005 |