Title: Appel's Salt
CAS Registry Number: 75318-43-3
CAS Name: 4,5-Dichloro-1,2,3-dithiazol-1-ium chloride
Molecular Formula: C2Cl3NS2
Molecular Weight: 208.52
Percent Composition: C 11.52%, Cl 51.01%, N 6.72%, S 30.75%
Literature References: Readily prepd from chloroacetonitrile and disulfur dichloride; 5-chloro position is reactive to nucleophilic substitution. Prepn: R. Appel et al., DE 2848221 (1980 to Bayer); eidem et al., Ber. 118, 1632 (1985). Synthetic applications: J. J. Folmer, S. M. Weinreb, Tetrahedron Lett. 34, 2737 (1993); A. M. Cuadro, J. Alvarez-Builla, Tetrahedron 50, 10037 (1994); G. L¢abbé et al., J. Chem. Soc. Perkin Trans. 1 1995, 2379; and crystal structure: C. W. Rees et al., ibid. 2002, 1535. Review of chemistry of polysulfur-nitrogen heterocycles: C. W. Rees, J. Heterocycl. Chem. 29, 639-651 (1992).
Properties: Pale yellow-green crystals, mp 172° (dec). Insol in organic solvents. Sensitive to water and other nucleophiles.
Melting point: mp 172° (dec)
Use: Synthon in heterocyclic chemistry; in conversion of alcohols and carboxylic acids to esters. |