J. Minamikawa

Syntheses and some properties of N-unsubstituted sulfilimines

Abstract A variety of S-aminosulfonium mesitylenesulfonates, R1R2S+NH2·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 Sue5f8N bond cleavage. The reactions of disulfides and thioketone with MSH are also described.

N-amination of tertiary amines : A novel method for 1,1,1-trisubstituted hydrazinium salts

Abstract A novel method for the preparation of 1,1,1-trisubstituted hydrazinium salts by the reaction with O-mesitylenesulfonylhydroxylamine (MSH) is described. The N-amine salts of some selected alkaloids were prepared. The stereochemistry of N-amination of securinine and allosecurinine with MSH was also investigated.