THE REACTION OF ALKANEPHOSPHONIC ACID ESTERS WITH METALS

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Abstract
The reaction of dialkyl alkanephosphonates (methyl, ethyl, isopropyl) with alkali and earth alkali metals, respectively, has been investigated. These metals reacted with phosphonates yielding the corresponding salts of monoalkyl alkanephosphonates with the evolution of a mixture of low molecular weight gaseous products the composition of which was quantitatively determined by gas chromatographic methods. The gaseous products could be traced to the primary formation of radical fragments originating from cleavage of either the carbon-oxygen or the phosphorus-oxygen bonds. Lower alkanes were formed predominantly, but there were also traces of acetylene and also of benzene. Diisopropyl methylphosphonate showed to a large extent cleavage of the carbon-phosphorus bond, yielding a mixture of the salts of isopropylphosphonite and isopropyl methylphosphonate. Reaction mechanisms were advanced to explain some of the results.

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