Trapping of thiaziridinimines with N‐sulfinylamines

Abstract
The reactions of 4‐alkyl‐5‐arylsulfonylimino‐1,2,3,4‐thiatriazolines with N‐sulfinylamines at 60‐70° yield 3‐oxo‐5‐arylsulfonylimino‐1,34,2,4‐dithiadiazolidines 4 which are smoothly converted by hydrolysis into S‐aminoisothio‐ureas 5. In contrast, the acetyl derivative 4g hydrolyzes into thiadiazoline 7. Structure assignment of the products was based on spectral and combustion analyses, chemical reactions, and, in the case of 4e, on an X‐ray structure determination.