Novel palladium(II)-catalyzed cyclization of aziridines and sulfur diimides

Article abstract of DOI:10.1021/ja00083a007

Bis(benzonitrile)palladium dichloride is an effective catalyst for the cyclization reaction of aziridines and sulfur diimides, in toluene, affording imidazolidinethiones in 52-70% yield. Reaction of an aziridine, labeled with ¹³C at one of the ring carbons, with a sulfur diimide resulted in incorporation of the label at the 2- and 5-positions of the imidazolidinethione. Thiazolidinimine formation results from the palladium(II)-catalyzed reaction of an aziridine with phenyl isothiocyanate.