Synthesis, Structure, and Reactivity of Metal Derivatives of Diethyl Ester of 1-Propynephosphonic Acid (1-DEPP)

Article abstract of DOI:10.1007/BF00903662

Metallation of diethyl ester of 1-propynephosphonic acid (1-DEPP) is achieved by treatment with alkaline amides, calcium amid and calcium in liquid ammonia, with isopropylmagnesium chloride in ether or via metal exchange from the potassium derivative of 1-DEPP with copper(II) and cobalt(II) chloride resp.On the basis of IR- and 1H-NMR-spectra the calcium derivative appears as a mixture of an allene and its isomeric acetylene.The IR-spectrum of the lithium derivative is consistent with an analogous phenomenon while an acetylene structure is attributed only to the cobalt and copper derivatives.The alkylation of the potassium derivative with alkyl halides and the hydroxyalkylation with benzaldehyde occur with low yield at the γ-position of the parent compound. - Key words: Allene-acetylene isomerization; Metal derivatives; Phosphonic acid derivatives