33. The Halide-Promoted Fragmentation of 1-Chloro-1-fluori-2(α-silylalkyl)cyclopropanes: A new entry to Fluorodienes

Article abstract of DOI:10.1002/hlca.19840670134

When heated in the presence of tetrabutylammonium fluoride or chloride, 1-chloro-1-fluoro-2-(trimethylsilyl)methyl-cyclopropanes (1,2, and 3) undergo smooth ringopening fragmentation to afford 2-fluoro-butadienes (4, 5 and 6, resp.)with high yields.Despite unfavorable geometries, the reaction is converted and the inversion mode of rotation dominates over the retention mode by y factor of roughly 100.