Preparation and Reactions of Perfluorohalogenoorganosulfenyl Halides

Abstract

Publisher Summary Perfluorohalogenoorganosdfenyl halides are, like thiols, mercaptides, and thioketones, key compounds for the synthesis of new perfluorohalogenoorganomercapto derivatives. The high reactivity of the S—X bond (X = C1, Br) toward electrophilic as well as nucleophilic reagents causes them to be highly valued starting materials for the synthesis of new derivatives. The chemistry of the not very stable sulfenyl fluorides has hardly been investigated. However, the easily accessible and relatively stable sulfenyl chlorides have been studied extensively. Particularly, worth mentioning is the application of sulfenyl compounds in plant preservation. Of primary importance in this respect are the reactions of sulfenyl chlorides with secondary amines, which with proper choice of the starting materials, lead to compounds with good fungicidal properties. The speed of the fluorine-chlorine exchange at the sulphur atom decreases with increasing degree of fluorination at the carbon atom. Compound CF3SF does not undergo exchange reactions at all; however, in the liquid phase it exists in equilibrium with the dimeric compound CF3SF2SCF3.