Cyanoethyl Thioethers

CAS 111-97-7 EINECS/ELINCS 203-926-5 Synonyms Bis (2-cyanoethyl) sulfide 2-Cyanoethyl thioether 3,3 -Thiodipropionitrile P,P-Thiodipropionitrile... 

Nitro displacement by 3-mercaptopropionitrile anion provides a new synthesis of 2-cyanophenyl thiocyanates (84). The intermediate cyanoethyl thioethers (83) are rapidly converted into the thiol anion via loss of acrylonitrile under the basic reaction conditions. Addition of cyanogen chloride then yields (84) (Scheme 47). 

The cyanobromide (371) was condensed with the bc portion (347) to give the thioether (372) sulfide contraction to give (373) was accomplished using tris(/3-cyanoethyl) phosphine, and with phosphorus pentasulfide the thiolactam-thiolactone (374) was produced. After treatment with Meerwein s salt, reaction with dimethylamine opened the lactone with concomitant formation of an exocyclic methylene group, and subsequent treatment with cobalt chloride or iodide gave the chelate (375) which was reacted with diazabicyclononane to give bisnorcobyrinic add [Pg.435]

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