4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's salt) is an
organosulfur compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
. It is the chloride salt of the 4,5-dichloro-1,2,3-dithiazolium cation. It is a green solid that is poorly soluble in organic solvents.
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Synthesis
The compound is obtained by the reaction of acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...
with sulfur monochloride
Disulfur dichloride (or disulphur dichloride by the British English spelling) is the inorganic compound of sulfur and chlorine with the formula . It is an amber oily liquid.
Sometimes, this compound is incorrectly named ''sulfur monochloride'' (o ...
. The initial phases of this reaction entail chlorination of the acetonitrile. The resulting dichloroacetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...
undergoes cycloaddition with sulfur monochloride:
:
The cation is highly electrophilic. It hydrolyzes readily. Protic nucleophiles displace one chloride:
:
The compound was discovered by Appel ''et al''.
References
{{DEFAULTSORT:Dichloro-1,2,3-dithiazolium chloride, 4,5-
Sulfur heterocycles
Nitrogen heterocycles
Heterocyclic compounds with 1 ring
Chlorides
Organochlorides
Sulfur–nitrogen compounds