Singlet Oxygen Production in the Reaction of Superoxide with Organic Peroxides

Laura A. MacManus-Spencer, Betsy L. Edhlund, and Kristopher McNeill*
University of Minnesota, Department of Chemistry, 207 Pleasant Street SE, Minneapolis, Minnesota 55455 mcneill@chem.umn.edu
J. Org. Chem., 2006, 71 (2), pp 796–799
DOI: 10.1021/jo051736n
Publication Date (Web): December 23, 2005
Copyright © 2006 American Chemical Society
*

 Corresponding author. Phone:  612-625-0781. Fax:  612-626-4751.

Abstract

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A selective chemiluminescent probe for singlet oxygen has been employed to detect and quantify singlet oxygen in the reactions of superoxide with organic peroxides. The production of singlet oxygen has been quantified in the reaction of superoxide with benzoyl peroxide (BP). No singlet oxygen was detected in the reactions of superoxide with cumyl peroxide, tert-butyl peroxide, or tert-butyl hydroperoxide. On the basis of these results and on the temperature dependence of the reaction, we proposed a mechanism for singlet oxygen formation in the reaction of superoxide with BP.

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History

  • Published In Issue January 20, 2006
  • Received August 17, 2005

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