Bimolecular Photoreduction of Aromatic Sulfoxides

Photolysis of aromatic sulfoxides in the presence of alkoxides in alcoholic solvents provides a photochemical route to the corresponding sulfides. Other electron donors also give sulfide with various degrees of success. The reaction could also be carried out using carbazoles as sensitizers, and quan...

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Veröffentlicht in:Journal of organic chemistry 2001-12, Vol.66 (25), p.8621-8628
Hauptverfasser: Cubbage, Jerry W, Tetzlaff, Troy A, Groundwater, Heather, McCulla, Ryan D, Nag, Mrinmoy, Jenks, William S
Format: Artikel
Sprache:eng
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Zusammenfassung:Photolysis of aromatic sulfoxides in the presence of alkoxides in alcoholic solvents provides a photochemical route to the corresponding sulfides. Other electron donors also give sulfide with various degrees of success. The reaction could also be carried out using carbazoles as sensitizers, and quantitative yields could be obtained using N-methylcarbazole in methanol. Evidence points toward a hydroxysulfuranyl radical as the key intermediate, and solvent effects point to heterolysis, rather than homolysis, as the step that breaks the S−O bond.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016134s