REGIOSELECTIVE OXIDATION AND HALOGENATION OF 2-(ARYLSULFENYLIMINO)-4-THIAZOLINE AND 2-(ARYLSULFINYLIMINO)-4-THIAZOLINE

The synthesis of 4-thiazoline 2-iminium sulfinates (3) is described. F rom the salts 3 and NBS the 2-(arylsulfonylimino)-4-thiazolines (4) we re formed, which have also been prepared by oxidation of 2-(arylsulfen ylimino)-4-thiazolines (5) and by reaction of the arylsulfonyl chlorid es (6) with 2-imino-4-thiazolines (2). The treatment of 5 with NBS (or NIS) in dry solvents results in 2-(arylsulfenylimino)-5-bromo (or iod o)-4-thiazolines (7); in the presence of NaHCO3 2-(arylsulfonylimino)- 5-bromo-4-thiazolines (8) are formed. 2-(Arylsulfinylimino)-4-thiazoli nes (10) have also been halo-genated in the same manner with NBS or NI S to give the products (11).