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Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines
The Journal of Organic Chemistry
  • Vasumathi Desikan, Iowa State University
  • Yonglin Liu, Johns Hopkins University
  • John P. Toscano, Johns Hopkins University
  • William S. Jenks, Iowa State University
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Time-resolved infrared (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene precursor, i.e., that the ground-state multiplicity is singlet. In contrast, product studies clearly indicate triplet reactivity for trifluoroacetylnitrene, though TRIR experiments were more ambiguous. Product studies suggest that these sulfilimines are superior sources for sulfonylnitrenes, which have triplet grounds states, to the corresponding azides, and computational studies shed light on the electronic structure of the nitrenes.

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 73(12); 4398-4414. Doi: 10.1021/jo702654q. Copyright 2008 American Chemical Society.

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Vasumathi Desikan, Yonglin Liu, John P. Toscano and William S. Jenks. "Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines" The Journal of Organic Chemistry Vol. 73 Iss. 12 (2008) p. 4398 - 4414
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