A simple method for the preparation of N-sulfonylsulfilimines from sulfides.
While excellent methods exist for the oxidation of sulfides to sulfoxides R1R2S-->R1R2SO, the azaversion of this atom transfer redox process, i.e., R1R2S-->R1R2S=N-SO2R3, has been less reliable. In sulfilimine synthesis, sulfoxide has been an inevitable byproduct in all cases to date, and the yields of sulfilimine have varied widely. A nearly ideal procedure for the sulfide to sulfonyl sulfilimine transformation is described. Almost quantitative yields are achieved from a diverse set of sulfides and a broad range of the readily available sulfonyl nitrenoid sources known as chloramine salts (R3SO2NClNa), essentially by simply stirring them together in acetonitrile.
Marzinzik
A L
AL
Department of Chemistry and Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 N, Torrey Pines Road, La Jolla, California 92037, USA.
Sharpless
K B
KB
D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry
D007097:Imines; D007202:Indicators and Reagents; D013440:Sulfides; D013454:Sulfoxides