Syntheses and some properties of N-unsubstituted sulfilimines

Abstract A variety of S-aminosulfonium mesitylenesulfonates, R 1 R 2 S + NH 2 ·X − , were prepared in high yields by the reaction of sulfides with O-mesitylenesulfonylhydroxylamine (MSH). The thermal stability of the derived sulfilimines was examined. Reaction of allyl sulfides with MSH afforded directly the salts of allylamines in good yields, presumably via [2,3]-sigmatropic rearrangement of unisolable allylsulfilimines followed by SN bond cleavage. The reactions of disulfides and thioketone with MSH are also described.