Trichloromethyl thioethers

An alternative to the synthesis of thioethers in which sulfur is a nucleophile, is a synthesis in which sulfur bears a leaving group. The reaction of a carbanion with a sul-fenyl halide should, in principle, constitute a synthesis of thioethers. Such a reaction of sulfenyl halides has not yet been reported but the case in which sulfur is rendered electrophilic by attached cyano, has been [10]. Thus, benzylthiocyanate reacts with trichloromethide ion (generated from chloroform under phase transfer conditions) according to equation 13.6 to yield (80%) of benzyl trichloromethyl thioether [10]. 

Bis(2-diisopropylaminoethyl) Disulfide Bis(2-diisopropylaminoethyl) Sulfide Bis(2-fluoroethyl) 2-Chloroethylamine Bis(2-fluoroethyl)methylamine Bis(2-hydroxyethyl) Sulfide Bis(2-hydroxyethyl) Thioether Bis(2-hydroxyethyl)amine Bis(2-hydroxyethyl)methylamine Bis(2-propenyl) Sulfide Bis(bromomethyl) Ether Bis(chloromethyl) Ether Bis(cyclohexyl)carbodiimide Bis(ethenyl)sulfone Bis(trichloromethyl) Carbonate Bis(/3-bromoethyl) Sulfide Bis(/3-chloroethyl)ethylamine Bis(/3-Chloroethyl)methylamine Bis(/3-chloroethylthio)ethane Bis(/3-mercaptoethyl) Sulfide... 

Trichloromethyl thioalkyl compounds of formula RSCXClj (a, b, X = Cl, R = Ph or CHjPh) as well as dichloromethyl benzyl thioether react with iron(II) tetraphenylporphyrin (TPP) (233), in the presence of a reducing agent (iron powder or Na2S204), to produce chlorocarbene complexes of type 234 (158). 

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