Synthesis of (p-Substituted-tetrafluorophenyl)ethynes and Diacetylene Monomers Containing Fluoro-Aromatic Rings by Nucleophilic Substitution on triethylsilane

Article abstract of DOI:10.1016/S0022-1139(00)80389-9

Substitutions on <(pentafluorophenyl)ethynyl>trimethylsilylsilane (1) with nucleophiles, Nu-X (2) give the corresponding <(p-substituted-tetrafluorophenyl)ethynyl>trimethylsilanes (3) or (p-substituted-tetrafluorophenyl)ethynes (4).The trimethylsilyl group of (3) can be easily removed by treatment with dilute alkali to give <(p-substituted-tetrafluorophenyl)-ethynes (4).Diacetylenes containing fluoro-aromatic rings are prepared by the Chodkiewiez-Cadiot and the Hay coupling of the corresponding terminal acetylenes (4).