Thioacyl chloride

In organic chemistry, a thioacyl chloride is an organic compound containing the functional group −C(=S)Cl. Their formula is usually written R−C(S)Cl, where R is a side chain. Thioacyl chlorides are analogous to acyl chlorides, but much rarer and less robust. Indeed, one of the simplest, thioacetyl chloride (c.f. acetyl chloride), remained unknown as of 1972.

Most thioacyl halides are "highly coloured, labile oils with pronounced pungent odours". Simple alkyl derivatives are volatile.

The best studied thioacyl chloride is thiobenzoyl chloride, a purple oil first prepared by chlorination of dithiobenzoic acid with a combination of chlorine and thionyl chloride. A more modern preparation employs phosgene as the chlorinating agent, by-producing carbonyl sulfide:

PhCS2H + COCl2 → PhC(S)Cl + HCl + COS

One example of a thioacyl chloride has been crystallized.

In general, thioacyl chlorides are produced from passing halocarbons through phosphorus pentasulfide or boiling sulfur. Such is the case for the simplest thioacyl chloride, thiophosgene. Thiocarbamyl and -carbonyl chlorides are prepared from the corresponding amines and alcohols by careful thiophosgenation.

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