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
Molecules 2005, 10(2), 346-359; https://doi.org/10.3390/10020346
Received: 29 November 2004
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Accepted: 16 December 2004
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Published: 28 February 2005
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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.
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Keywords:
1; 2; 3-Dithiazole; 1; 2; 5-thiadiazole; heterocycle; heteroaromatic; electro- chemistry.
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MDPI and ACS Style
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. https://doi.org/10.3390/10020346
AMA Style
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(2):346-359. https://doi.org/10.3390/10020346
Chicago/Turabian StyleKoutentis, P. 2005. "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 10, no. 2: 346-359. https://doi.org/10.3390/10020346
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