Reactivity of a 1-germapropadiene

alpha-Lithiofluorogermane 3 eliminated lithium fluoride to give 1-germaprop adiene 1 even at -75 degrees C. The reactivity of 1-germapropadiene 1 was i nvestigated. Compound 1 was not stable above 0 degrees C in solution or 90 degrees C in the solid state. Two C-H insertion cyclic compounds, 8 and 9, were formed as a result of decomposition. Water, methanol, and ethanol adde d across the Ge=C double bond of 1 to give vinylalkoxy (hydroxy) germanes, Benzophenone did not react with 1 at 0 degrees C, but benzaldehyde gave oxa germetane 13 in good yield. When acetone was introduced to 1, it gave the u nexpected product 10, the water adduct.