A general facile preparation of F-alkylacetylenes

Article abstract of DOI:10.1016/S0022-1139(00)85065-4

F-Alkylethylenes can be exhaustively chlorinated under UV irradiation to give F-alkylpentachloroethanes in high yields. Subsequent dechlorination with three equivalents of zinc readily gives the F-alkylacetylenic zinc reagents, which on hydrolysis with aqueous HCl provide the corresponding F-alkylacetylenes in good yields. The methodology is applicable to F-alkyl groups of various chain lengths, and the F-acetylenic zinc reagent produced as the reaction intermediate can also be utilized in the direct preparation of functionalized F-alkylacetylenes.