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Sulfenyl chloride

Chemical group (R–S–Cl)

Chemical group (R–S–Cl)

In organosulfur chemistry, a sulfenyl chloride is a functional group with the connectivity , where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of . They are used in the formation of and bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.

Typically, sulfenyl halides are stabilized by electronegative substituents. This trend is illustrated by the stability of obtained by chlorination of carbon disulfide.

Preparation

Sulfenyl chlorides are typically prepared by chlorination of disulfides:

:

This reaction is sometimes called the Zincke disulfide reaction, in recognition of Theodor Zincke.{{cite journal

Some thioethers () with electron-withdrawing substituents undergo chlorinolysis of a bond to afford the sulfenyl chloride.

In a variation on the Reed reaction, sulfur dichloride displaces hydrogen under UV light.

Reactions

Perchloromethyl mercaptan () reacts with bonds in the presence of base to give the sulfenamides: : This method is used in the production of the fungicides Captan and Folpet.

Sulfenyl chlorides add across alkenes, for example cyclohexene and ethylene :

They undergo chlorination to the trichlorides: :

Sulfenyl chlorides react with water and alcohols to give sulfenyl esters (): : :

Route to sulfinyl halides

Sulfenyl chlorides can be converted to sulfinyl chlorides (RS(O)Cl). In one approach, the sulfinyl chloride is generated in two steps starting with reaction of a thiol () with sulfuryl chloride (). 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:

:[[File:Conversion of F3CCPh2SH to F3CCPh2SCl and on to F3CCPh2S(O)Cl.png|frameless|600px|left]]

References

References

  1. {{ cite book. (2008). "Alkanesulfenyl Halides"
  2. Hubacher, Max H.. (1943). "''o''-Nitrophenylsulfur chloride".
  3. (1973). "Methanesulfinyl Chloride".
  4. F. B. Wells, C. F. H. Allen. (1935). "2,4-Dinitroaniline". Organic Syntheses.
  5. Norman Kharasch, Robert B. Langford. (1964). "2,4-Dinitrobenzenesulfenyl Chloride". Organic Syntheses.
  6. Smith (2020), ''March's Organic Chemistry'', rxn. 14-9.
  7. (2007). "Encyclopedia of Reagents for Organic Synthesis".
  8. (1954). "Synthesen mit Alkylschwefelchloriden (X. Mitteil. über organische Schwefelchloride)". Chemische Berichte.
  9. (2005). "Phenylsulfenylation of Nonactivated Carbon Atom by Photolysiis of Alkyl Benzenesulfenated: Preparation of 2-Phenylthio-5-heptanol". Organic Syntheses.
  10. (1995). "Synthesis: Carbon with One Heteroatom Attached by a Single Bond". [[Elsevier]].
  11. Danehy, James P.. (1971). "Sulfur in Organic and Inorganic Chemistry". Marcel Dekker.
  12. (2009). "Stable Sulfenyl Iodide Bearing a Primary Alkyl Steric Protection Group with a Cavity-shaped Framework". Chemistry Letters.
  13. (2008). "Alkylsulfur Trihalides". Sci. Synth..
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organosulfur-compounds functional-groups sulfenyl-chlorides
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