Mechanism of asymmetric sulfimidation with N-alkoxycarbonyl azide in the presence of (OC)Ru(salen) complex

Spectroscopic analysis of imidation of alkyl aryl Sulfides with N-2,2,2-trichloro-1,1-diniethylethyloxycarbonyl azide 2 in the presence of (OC)Ru(salen) complex 1 strongly suggests that an addition compound of the azide 2 to 1 is the active species for the imidation, while the addition compound undergoes the undesired intrarnolecular C-H insertion onto the salen ligand of the complex in the absence of sulfide, directly or via the corresponding nitrene-ruthenium Species. (C) 2003 Elsevier Ltd. All rights reserved.