27.4.3 Thioaldehyde and Thioketone S-Oxides and S-Imides (Sulfines and Derivatives) (Update 2014)

G. Mlostoń; H. Heimgartner

Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods of synthesis and new applications for thiocarbonyl S-oxides (sulfines) and thiocarbonyl S-imides. In general, thiocarbonyl S-oxides are more stable and in many instances can be isolated. The in situ generated thiocarbonyl S-imides are efficient “sulfur-transfer agents” via the isomeric thiaziridines, formed as products of electrocyclic ring closure. Stable thiocarbonyl S-imides, derived from hexafluorothioacetone, are useful 1,3-dipoles and are applied in the preparation of fluorinated five-membered heterocycles.

Key words

thiazolidines - cycloaddition - five-membered rings - oxidation - small-ring systems - thiones

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