Thioacyl chloride

In organic chemistry, thioacyl chloride is a functional group of the type RC(S)Cl, where R is an organic substituent. Thioacyl chlorides are analogous to acid chlorides, but much rarer and less robust. The best studied is thiobenzoyl chloride, a purple oil first prepared by chlorination of dithiobenzoic acid with a combination of chlorine and thionyl chloride.[1] A more modern preparation employs phosgene as the chlorinating agent,[2] this also generates carbonyl sulfide as a by-product.

PhCS₂H + COCl₂ → PhC(S)Cl + HCl + COS

The compounds are more stable with electron-releasing substituents.

References

Staudinger, H.; Siegwart, J. (1920). "Ueber Thiobenzoylchlorid" [Thiobenzoyl chloride] (PDF). Helvetica Chimica Acta. 3: 824–33. doi:10.1002/hlca.19200030177.CS1 maint: uses authors parameter (link)
Viola, H.;Mayer, R. (1975). "Eine neue Darstellungsmethode für aromatische Thiocarbonsäurechloride" [A New Preparation Route for Aromatic Thiocarboxylic Acid Chlorides]. Z. Chem. 15: 348. doi:10.1002/zfch.19750150904.CS1 maint: uses authors parameter (link)

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[1] Staudinger, H.; Siegwart, J. (1920). "Ueber Thiobenzoylchlorid" [Thiobenzoyl chloride] (PDF). Helvetica Chimica Acta. 3: 824–33. doi:10.1002/hlca.19200030177.CS1 maint: uses authors parameter (link)

[2] Viola, H.;Mayer, R. (1975). "Eine neue Darstellungsmethode für aromatische Thiocarbonsäurechloride" [A New Preparation Route for Aromatic Thiocarboxylic Acid Chlorides]. Z. Chem. 15: 348. doi:10.1002/zfch.19750150904.CS1 maint: uses authors parameter (link)