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.
^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.
thioacylchloride is a functional group of the type RC(S)Cl, where R is an organic substituent. Thioacylchlorides are analogous to acid chlorides, but...
C6H5C(S)OCH3. Such compounds are typically prepared by the reaction of the thioacylchloride with an alcohol. They can also be made by the reaction of Lawesson's...
Fe(S2CC6H5)3 and Ni(S2CC6H5)2. Chlorination of dithiobenzoic acid gives the thioacylchloride C6H5C(S)Cl. M. R. Crampton (1974). "Acidity and hydrogen-bonding"...