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Deoxygenation and Other Photochemical Reactions of Aromatic Selenoxides1
Journal of the American Chemical Soiety
  • Ryan D. McCulla, Iowa State University
  • William S. Jenks, Iowa State University
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Atomic oxygen O(3P) is a potent oxidant that has been well-studied in the gas phase. However, exploration of its reactivity in the condensed organic phase has been hampered by the lack of an appropriate source. Dibenzothiophene-S-oxide (DBTO) and related derivatives have been promoted as photochemical O(3P) sources but suffer from low quantum yields. Photolysis of dibenzoselenophene-Se-oxide (DBSeO) results in the formation of dibenzoselenophene and oxidized solvent in significantly higher quantum yields, ca. 0.1. The oxidation product ratios from toluene obtained from the photolysis of dibenzothiophene-S-oxide and the corresponding selenoxide are the same, strongly suggesting a common oxidizing intermediate, which is taken to be O(3P). An additional product, proposed to be the corresponding selenenic ester, is also observed under deoxygenated conditions. The photochemistry of diphenyl selenoxide includes a minor portion of oxidant-forming deoxygenation, in contrast to previous conclusions (Yamazaki, Y.; Tsuchiya, T.; Hasegawa, T.Bull. Chem. Soc. Jpn. 2003, 201−202).

Reprinted (adapted) with permission from Journal of the American Chemical Society; 126(49); 16058-16065. Doi: 10.1021/ja045935k. Copyright 2004 American Chemical Society.

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American Chemical Society
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Ryan D. McCulla and William S. Jenks. "Deoxygenation and Other Photochemical Reactions of Aromatic Selenoxides1" Journal of the American Chemical Soiety Vol. 126 Iss. 49 (2004) p. 16058 - 16065
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