On alkylideneamidosulfenyl chlorides and 1-Thia-2-azoniaallene salts

X-Ray-diffraction analysis of tBu2CNSCl (4b) revealed an almost linear CNS unit with an SN bond order of ca. 1.9 (Fig. 1), in agreement with the structure of a 1-thia-2-azoniaallene chloride. With SCl2 and SbCl5, compound 4b was transformed into the imidosulfurous dichloride 6 (Scheme 2). With morpholine, compounds 4b and 6 afforded the sulfenamide 7and the aminosulfonium salt 8, respectively. The (diarylmethylene)amidosulfenyl chlorides 4g,h,i reacted with SbCl5 to give SbCl salts of the 1,2-benzisothiazoles 9a,b,d, most likely via 1-thia-2-azoniaallene intermediates 2 (Scheme 3).