Arenethiosulfenyl chlorides

A more promising method involves the use of arenethiosulfenyl chlorides. These reagents oxidize alkenes to a-chloro-p-disulfidearenes (i.e. 2) in high yields. The intermediates are then reduced by sodium sulfide and cyclized to thiiranes in good to moderate yield. Unfortunately these arenethiosulfenyl chlorides must be prepared fix>m arenethiols and sulfur dichloride nevertheless, the yields of acyclic adducts are reliably mo(lerate. In addition, the arene substituents may be changed to modify the nuckophil-icity and reducibility of the reagent. ... 

For the formation of thiiranes from alkenes, it seems best to use the arenethiosulfenyl chloride method since this appears to result in the highest yields. While the sulfur monochloride method can be used, the yields are ically poor to moderate over a wide range of substrates. For both methods there are some common problems which include competing group reactivity (other alkenes or electron-rich groups) and, of course, the stench associated with many sulfides. 

---