Uses
Phenylsulfenyl Chloride is an intermediate used in the synthesis of Tabanone (T003450), which is found in oils of Trifolium pratense L. and is a potential natural anti-oxidant.
Preparation
To a flask containing 32.7 gm (0.15 mole) of diphenyl disulfide dissolved in 100 ml of dichloromethane containing 3 ml of pyridine is slowly dropwise added at room temperature 20.3 gm (0.15 mole) of freshly distilled sulfuryl chloride. After completion of the addition, the solution is stirred for an additional hour, concentrated under reduced pressure (12 mm Hg) at 25°C, and the residue distilled to afford 33 gm (76%), b.p. 49°C (4 mm Hg), of a dark red liquid.
Precautions
Phenylsulfenylchloride is extremely hygroscopic and must be carefully protected from moisture. It may be stored for months under dry inert gas in a refrigerator. However, there are two reports on the spontaneous explosion of PhSCl on storage, even in a refrigerator. It is recommended that PhSCl be prepared fresh as needed. Use in a fume hood.
