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
- ^ "Ueber Thiobenzoylchlorid" [Thiobenzoyl chloride] (PDF). Helvetica Chimica Acta. 3: 824–33. 1920. doi:10.1002/hlca.19200030177.
{{cite journal}}: Unknown parameter|authors=ignored (help) - ^ "Eine neue Darstellungsmethode für aromatische Thiocarbonsäurechloride" [A New Preparation Route for Aromatic Thiocarboxylic Acid Chlorides]. Z. Chem. 15: 348. 1975. doi:10.1002/zfch.19750150904.
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