4,5-Dichloro-1,2,3-dithiazolium chloride

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4,5-Dichloro-1,2,3-dithiazolium chloride
Names
Other names
Appel's salt
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C2Cl2NS2.ClH/c3-1-2(4)6-7-5-1;/h;1H/q+1;/p-1
    Key: NIZMCFUMSHISLW-UHFFFAOYSA-M
  • C1(=NS[S+]=C1Cl)Cl.[Cl-]
Properties
C2Cl3NS2
Molar mass 208.50 g·mol−1
Appearance green solid
Melting point 172 °C (342 °F; 445 K) decomposition
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's salt) is an organosulfur compound. 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.[1]

Synthesis

The compound is obtained by the reaction of acetonitrile with sulfur monochloride. The initial phases of this reaction entail chlorination of the acetonitrile. The resulting dichloroacetonitrile undergoes cycloaddition with sulfur monochloride:[1]

Cl2CHCN + S2Cl2 → [S2NC2Cl2]Cl + HCl

The cation is highly electrophilic. It hydrolyzes readily. Protic nucleophiles displace one chloride:[2][3]

[S2NC2Cl2]Cl + 2 RNH2 → S2NC2Cl(=NR) + [RNH3]Cl

The compound was discovered by Appel et al.[4]

References

  1. ^ a b Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. doi:10.1002/jhet.5570290306.
  2. ^ Foucourt, Alicia; Chosson, Elizabeth; Besson, Thierry (2009). "4,5-Dichloro-1,2,3-dithiazol-1-ium Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01113. ISBN 978-0471936237.
  3. ^ Cuadro, Ana M.; Alvarez-Buila, Julio (1994). "4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's Salt): Reactions with N-Nucleophiles". Tetrahedron. 50 (33): 10037–10046. doi:10.1016/S0040-4020(01)89619-8. hdl:10017/3581.
  4. ^ Appel, Rolf; Janssen, Heinrich; Siray, Mustafa; Knoch, Falk (1985). "Synthese und Reaktionen des 4,5-Dichlor-1,2,3-dithiazolium-chlorids". Chemische Berichte. 118 (4): 1632–1643. doi:10.1002/cber.19851180430.
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