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- W3092292144 abstract "ortho-Quinone methides, very reactive transient intermediates, are utilized successfully in synthesizing complex organic molecules of natural and biological significance. Among several synthetic protocols, the acid catalyzed generation of ortho-quinone methides from suitably substituted phenols is a promising method for further exploitation in organic synthesis. Such an interesting reactive species is conveniently employed in the synthesis of conformationally restricted triarylmethane derivatives such as 12/9-arylxanthenes/arylthioxanthenes starting from symmetrical/unsymmetrical 2-(hydroxydiarylmethyl)phenol/thiophenol, respectively, using SiO2-NaHSO4. Conformationally restricted 12/9-arylxanthenes/arylthioxanthenes were obtained in 52 to 96% yields using this protocol, which is believed to involve the formation of o-quinone methides followed by electrocyclic ring closure and isomerization at elevated temperature. Photophysical studies of selected examples in acidic media showed turn-on fluorescence by hydride ion transfer mediated π-conjugated xanthylium salt formation and suggested the application potential in bio-imaging and fluorescent sensors." @default.
- W3092292144 created "2020-10-15" @default.
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- W3092292144 creator A5059504646 @default.
- W3092292144 date "2020-01-01" @default.
- W3092292144 modified "2023-09-27" @default.
- W3092292144 title "NaHSO<sub>4</sub>/SiO<sub>2</sub> catalyzed generation of <i>o</i>-quinone/ <i>o</i>-thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes <i>via</i> oxa-6π-electrocyclization" @default.
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- W3092292144 doi "https://doi.org/10.1039/d0ob01868f" @default.
- W3092292144 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33073833" @default.
- W3092292144 hasPublicationYear "2020" @default.
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