Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines

• DOI: 10.1021/jo702654q
• Publication Date: 2008-05-29T08:01:58Z
• Authors: Vasumathi Desikan; Yonglin Liu; John P. Toscano; William S. Jenks
• Keywords: Nitrene; Reactivity; Dibenzothiophene

Time-resolved infrared (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that expected release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, tosylnitrene. All three provided results for acetylnitrene consistent with literature precedent analogous experiments benzoylnitrene precursor, i.e., ground-state multiplicity is singlet. In contrast, studies clearly indicate triplet reactivity though TRIR more ambiguous. Product suggest these are superior sources sulfonylnitrenes, which have grounds states, corresponding azides, shed light on electronic structure nitrenes.