Cyclopropylidene lithium carbenoids reacted with bis(pinacolato)diboron in THF/Et2O at -110 degrees C to give various 1,1-diborylated cyclopropanes in good yields. Treatment of the diborylated cyclopropanes with 3-chloro-1-lithio-3-methyl-1-butyne produced the corresponding diborylated allenylcyclopropanes, which underwent ring-expansion in the presence of a Rh catalyst to give 1,2-diborylated methylenecyclopentenes conveniently.