Sulfenyl chloride
A sulfenyl chloride is a functional group with the connectivity R–S–Cl, where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of RS+. They are used in the formation of RS–N and RS–O bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.
Sulfenyl chlorides are typically prepared by chlorination of disulfides:
This reaction is sometimes called the Zincke disulfide reaction, in recognition of Theodor Zincke. Typically, sulfenyl halides are stabilized by electronegative substituents. This trend is illustrated by the stability of CCl3SCl obtained by chlorination of carbon disulfide.
A general approach to the formation of sulfinyl chlorides, RS(O)Cl, is by reaction of the corresponding thiol with sulfuryl chloride, SO
2Cl
2, but in some cases the sulfenyl chloride results instead, as happens with 2,2,2-trifluoro-1,1-diphenylethanethiol. A trifluoroperacetic acid oxidation then provides a general approach to formation of sulfinyl chlorides from sulfenyl chlorides:
CCl3SCl reacts with N-H-containing compounds in the presence of base to give the sulfenamides:
This method is used in the production of the fungicide captan.
Sulfenyl chlorides add across alkenes:
They undergo chlorination to the trichlorides:
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