Phenylsulfenylchloride

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 1208, 1978 DOI: 10.1021/jo00400a041
Chemical and Pharmaceutical Bulletin, 28, p. 126, 1980 DOI: 10.1248/cpb.28.126