Comparative study of metal-catalyzed iminations of sulfoxides and sulfides.

A comparative study of the imination of sulfur compounds with various metal catalysts in combination with isolated or in situ generated iminoiodinanes (PhI==NR) as nitrogen sources is presented. The influence of the metal catalyst towards the imination of a variety of substituted sulfoxides has been evaluated. Moreover, the effect of the different oxidation states of sulfur on the reactivity and selectivity of the nitrogen transfer redox process in the formation of sulfilimines and sulfoximines was studied. Depending on both the specific metal catalyst as well as the employed nitrene precursor, the sulfide/sulfoxide imination ratio varied in transformations of thianthrene-5-oxide and substituted para-thio phenylsulfoxides.