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Article
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
Document Type
Article
Publication Version
Published Version
Publication Date
11-19-2004
DOI
10.1021/ja045935k
Abstract

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).

Comments

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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Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
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
Available at: http://works.bepress.com/william_jenks/6/