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Experimental and Computational Evidence for the Formation of Iminopersulfinic Acids

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  • Edward L. Clennan, University of Wyoming
  • ,
  • Ming-Fang Chen, University of Wyoming
  • ,
  • Alexander Greer, University of Wyoming
  • ,
  • F. Jensen
An experimental and computational study of the reactions of singlet oxygen with N-substituted sulfenamides is reported. Intermediates capable of epoxidizing norbornene were observed during the photooxidations of three sulfenamides. These results are used to argue for formation of iminopersulfinic acids. The structural integrity of two iminopersulfinic acids was supported by their successful location at the MP2/6-31G* level of theory. Furthermore, the inability to locate computationally significant persulfinimide precursors suggests that the iminopersulfinic acids form by enelike reactions involving near-simultaneous addition of singlet oxygen to sulfur and hydrogen abstraction.
Original languageEnglish
JournalJournal of Organic Chemistry
Pages (from-to)3397-3402
Number of pages6
Publication statusPublished - 1998
Externally publishedYes

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