Preparation of Sulfides From Thiocyanates

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]. 

The results of this and related reactions involving chloroform [10], phenylacetoni-trile [10], and phenylacetylene [11] are recorded in Table 13.3. 

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