Reactions of Bielectrophiles (ClCH₂CH₂)₂Y with Sulfur in Basic Reducing Systems

A simple procedure was developed for preparing bis(β-mercaptoethyl) ether and bis(β-ecraptoethyl) sulfide from commercially available chemicals: elemental sulfur, alkali, and bis(β-chloroethyl) ether or sulfide, based on thiylation with elemental sulfur of these substrates in the aqueous system hydrazine hydratealkali, with initial formation of the corresponding polysulfide polymers (thiokols). Their reduction with the system hydrazine hydrate-alkali, followed by acidification of dithiolate anions, yields the corresponding dithiols. Thiokols based on bis(β-chloroethyl) ether are soluble in organic solvents; they were studied by ¹H NMR.