Synthesis of Heterocycles From Thio- and Selenocarbonyl Compounds

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

Keywords:

• Thioketone
• sulfine
• thiosulfine
• trithiolane
• selenoketone
• α-dithiolactone