Thiuram disulfides are a class of organosulfur compounds with the formula (R2NCSS)2. Many examples are known, but popular ones include R = Me and Et. They are disulfides obtained by oxidation of the dithiocarbamates. These compounds are used in sulfur vulcanization of rubber as well as pesticides and drugs. They are typically white or pale yellow solids that are soluble in organic solvents.
Preparation, structure, reactions
- 2 R2NCSSNa + Cl2 → (R2NCSS)2 + 2 NaCl
- [Me2NC(S)S]2 + MeMgX → Me2NC(S)SMe + Me2NCS2MgX
The compounds feature planar dithiocarbamate subunits and are linked by an S−S bond of 2.00 Å. The C(S)−N bond is short (1.33 Å), indicative of multiple bonding. The dihedral angle between the two dithiocarbamate subunits approaches 90°.
- (R2NCSS)2 + PPh3 → (R2NCS)2S + SPPh3
The tetramethyl derivative, known as thiram, is a widely used fungicide. The tetraethyl derivative, known as disulfiram, is commonly used to treat chronic alcoholism. It produces an acute sensitivity to alcohol ingestion by blocking acetaldehyde dehydrogenase conversion of acetaldehyde leading to a higher concentration of the aldehyde in the blood producing symptoms of a severe hangover.
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