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Molecules 2005, 10(2), 346-359; doi:10.3390/10020346
Article

The Preparation and Characterization of 5-Substituted-4-chloro-1,2,3-dithiazolium Salts and their Conversion into 4-Substituted-3-chloro-1,2,5-thiadiazoles

Department of Chemistry, University of Cyprus, Cyprus
Received: 29 November 2004 / Accepted: 16 December 2004 / Published: 28 February 2005
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Abstract

A series of monosubstituted acetonitriles were treated with disulfur dichloride atroom temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1.Where the 5-substituent was not a good leaving group the chloride salts were converted intothe corresponding perchlorate salts 2 which were sufficiently stable and soluble to provideboth 1H- and 13C-NMR and cyclic voltammetry data. Several of the dithiazolium chlorideswere converted into their corresponding 4-substituted-3-chloro-1,2,5-thiadiazoles 13 ontreatment with aqueous ammonia. Mechanisms for all reactions are proposed.
Keywords: 1; 2; 3-Dithiazole; 1; 2; 5-thiadiazole; heterocycle; heteroaromatic; electro- chemistry. 1; 2; 3-Dithiazole; 1; 2; 5-thiadiazole; heterocycle; heteroaromatic; electro- chemistry.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Koutentis, P. The Preparation and Characterization of 5-Substituted-4-chloro-1,2,3-dithiazolium Salts and their Conversion into 4-Substituted-3-chloro-1,2,5-thiadiazoles. Molecules 2005, 10, 346-359.

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