Fluoride ion mediated reactions of disubstituted acetylenes Me3SiCCMMe3 (M=C, Si, Ge, Sn) with terminal acetylenes

The CsF–18-crown-6 mediated reactions of disubstituted acetylenes Me3SiCCMMe3 (M=C, Si, Ge, Sn) with phenylacetylene and 2-methyl-5-pyridylacetylene in benzene have been studied. The first step of the reaction is the deprotonation of aryl acetylene by F−-ion. The carbanion formed interacts with the disubstituted acetylene. The silylated, germylated and stannylated acetylenes were formed in yields 26–91%. Quantum chemical calculations of trimethylsilyl and trimethylgermyl group transfer have been performed.