Three types of ring-opening reactions of gem-difluorocyclopropyl carbinols are described ; 1) reaction with hydrobromic acid, 2) reaction with acetic acid in the presence of p-toluenesulfonic acid, and 3) rearrangement through a mesylate. Ring-opening reactions of 1a, d, e having an electron-donating substituent at C₃ were found to give β, β-difluorohomoallyl derivatives derived from C₁-C₃ bond scission. On the other hand, reactions of 1b, c having hydrogen atoms or a methyl group at C₃ were not selective or afforded α, α-difluorohomoallyl derivatives (C₁-C₂ bond scission) preferentially.