Selective C-mono- and C, C-dialkylation of thiophosphorylacetonitriles

Article abstract of DOI:10.1007/BF02498169

Alkylation of thiophosphorylacetonitriles under phase transfer catalysis conditions in the 50% NaOH/CH₂Cl₂ system proceeds as monoalkylation, whereas alkylation in MeCN with the use of solid KOH as a base gives a disubstituted product. The order in which the reagents were added as well as dilution of the reaction mixture affected substantially the yields of the target compounds. X-ray diffraction analysis of a single crystal of dibutyl(diphenylthiopliosphoryl)acetonitrile was carried out.