フルオロアセチレンの化学と合成化学的展開

概要

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Fluoroacetylene, an interesting haloacetylene, has not received much attention due to its instability and/or explosive nature. In addition, only a few fluoroacetylene derivatives have been reported so far. We have been interested in preparation of easy-handling fluoroacetylene compounds and demonstration of their utilization as a mono-fluorinated versatile building block. This article mainly deals with the following topics. 1) Fluoro(triisopropylsilyl)acetylene was easily prepared from 1,1-difluoroethylene in high yield and its 13C NMR spectrum was recorded for the first time. 2) The spontaneous trimerization of the fluoroacetylene afforded the corresponding fluorinated Dewar benzene instead of fluorinated crowded benzene. 3) Fluoro(silyl or stannyl)acetylenes except for fluoro(triisopropylsilyl)acetylene underwent radical addition reaction with THF to give the β-fluoro-β-(tetrahydrofuran-2-yl)vinylsilanes. 4) Fluoro(silyl or stannyl)acetylenes were easily transformed into the corresponding 4-fluoropyrazoles regioselectively, which functioned as a versatile 4-fluoropyrazole scaffold.