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

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