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]^[2] A more modern preparation employs phosgene as the chlorinating agent,^[3] this also generates carbonyl sulfide as a by-product.

PhCS₂H + COCl₂ → PhC(S)Cl + HCl + COS The most common thioacyl chloride is thiophosgene.

References

^ Hermann Staudinger; Siegwart, J. (1920). "Ueber Thiobenzoylchlorid" [Thiobenzoyl chloride]. Helvetica Chimica Acta. 3: 824–833. doi:10.1002/hlca.19200030177.
^ Potts KT, Sapino C (1972). "Thiocarbonyl halides". In Saul Patai (ed.). Acyl Halides. PATAI'S Chemistry of Functional Groups. pp. 349–380. doi:10.1002/9780470771273.ch11. ISBN 9780470771273.
^ Viola H, Mayer R (1975). "Eine neue Darstellungsmethode für aromatische Thiocarbonsäurechloride" [A New Preparation Route for Aromatic Thiocarboxylic Acid Chlorides]. Z. Chem. 15 (9): 348. doi:10.1002/zfch.19750150904.

[1] Hermann Staudinger; Siegwart, J. (1920). "Ueber Thiobenzoylchlorid" [Thiobenzoyl chloride]. Helvetica Chimica Acta. 3: 824–833. doi:10.1002/hlca.19200030177.

[Patai-2] Potts KT, Sapino C (1972). "Thiocarbonyl halides". In Saul Patai (ed.). Acyl Halides. PATAI'S Chemistry of Functional Groups. pp. 349–380. doi:10.1002/9780470771273.ch11. ISBN 9780470771273.

[3] Viola H, Mayer R (1975). "Eine neue Darstellungsmethode für aromatische Thiocarbonsäurechloride" [A New Preparation Route for Aromatic Thiocarboxylic Acid Chlorides]. Z. Chem. 15 (9): 348. doi:10.1002/zfch.19750150904.

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