Dec 27, 2017
Preparation of phenylsulfenyl chloride from diphenyl disulfide and chlorine.
It is a quite easy preparation of the highly reactive PhSCl when we add the non odorous diphenyl disulfide (PhSSPh) to an aprotic solvent, like chloroform or hexanes and absorb some chlorine it it. As the chlorine is absorbed to the solvent, the poorly soluble disulfide dissolved and gives a deep orangeish-red solution contains some excess chlorine, and the preferred sulfenyl chloride.
What happens here? This: R2S2 + Cl2 → 2 RSCl in this case R is an aromatic ring.
Important to note that chlorine is HIGHLY toxic and as a safer alternative N-chlorosuccinimide could be also used.