Author:
MacDonald J. W.,McKinnon D. M.
Abstract
5-Aryl-1,2,4-dithiazole-3-thiones may be made by sulfurization of N-aroyl-isothiocyanates, -thionocarbamates, or -dithiocarbamates. Attempts to produce 5-alkyl compounds failed, whereas an alternate cyclization of a reaction intermediate produced a 1,3-thiazine from cinnamoyl isothiocyanate. The mechanisms of the reactions are discussed briefly. The thiones readily form adducts with methyl iodide and reactive acetylenes. In the latter case, 1,3-dithiole derivatives are obtained.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
21 articles.
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1. 1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(iii) compounds – a kinetic comparative study;Organic & Biomolecular Chemistry;2012
2. Unusual conversion of substituted-3-formylchromones to 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones: a facile and efficient route to novel 1,2,4-dithiazoles;Tetrahedron Letters;2008-01
3. Ring Transformations of 1,2,4-Dithiazoles: Synthesis and Biological Studies of Novel S-Heterocycles, and Their Relevant Phosphono Derivatives;Zeitschrift für Naturforschung B;2007-01-01
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5. Ring-Opening Insertion of a Substituted Dithiazole-3-thione into the Re−Re Bond in a Dirhenium Carbonyl Complex;Organometallics;1996-04-16