The Selective C-Mono-and C,C-Dialkylation of Thiophosphorylacetonitriles and Reactivity of the Products

The facile synthetic route to selective C-mono-and C,C-dialkylation of thiophosphorylacetonitriles by primary haloalkanes under phase transfer catalysis conditions has been developed. Using under the same conditions unsymmetric alpha,omega-dihaloalkanes results in different linear and cyclic products depending on the alkylene chain length. 3-Halopropylsubstituted thiophosphorylacetonitriles synthesized transform to mono-and bis-heterophosphacyclanes under elevated temperatures.