N. Ohtani et al., Thiocyanation of alkyl halides with alkyl thiocyanates in the presence of quaternary phosphonium halides, J CHEM S P2, (9), 2000, pp. 1851-1856
Citations number
14
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Alkyl thiocyanates undergo simple S(N)2 reactions with the counter ions of
quaternary phosphonium salts in nonpolar solvents and thiocyanate ions are
liberated as the leaving ion. Depending on the nucleophile, the reaction pr
oceeded irreversibly or reversibly. The reaction of benzyl thiocyanate with
azide ions afforded a quantitative yield of benzyl azide. The reactions of
alkyl thiocyanates with halide ions gave an equilibrium mixture where the
reverse reaction of the alkyl halides produced with the liberated thiocyana
te ions took place simultaneously. Thus, thiocyanate-halide exchange reacti
ons between an alkyl thiocyanate and an alkyl halide were possible in the p
resence of a catalytic amount of a quaternary salt.