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Original Articles

Synthesis of Heterocycles From Thio- and Selenocarbonyl Compounds

Pages 340-348 | Received 10 Sep 2012, Accepted 12 Sep 2012, Published online: 29 May 2013
 

abstract

Reactions of thioketones, sulfines, and thiosulfines were reviewed. Thioaldehydes and thioketones were formed by the reaction of phosphonium ylides with elemental sulfur. Prolonged heating of this reaction resulted in the formation of thiosulfine intermediates, which were treated with DMAD or thiones to give the corresponding adducts. Selenocarbonyl compounds were also formed by this method. α-Dithiolactone was synthesized by the reaction of di-tert-butylthioketene S-oxide with Lawesson's reagent. α-Disulfines were isolated by the reaction of thiocamphor derivatives with S2Cl2 followed by oxidation.

GRAPHICAL ABSTRACT

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