Metalated methylenediphosphonate esters. Preparation, characterization and synthetic applications

Add time:09/24/2019    Source:sciencedirect.com

The metalation of esters of tetraalkyl methylenediphosphonates with sodium, potassium, sodium hydride and n-butyllithium to form the corresponding salts, M+[CH(PO3R2)2], is described. These compounds were characterized by 31P and 1H NMR; their synthetic usefulness was demonstrated by the preparation of a variety of alkylates, R′CH(PO3R2)2, and by the preparation of mono and dihalo derivatives, XCH(PO3R2)2 and X2C(PO3R2)2, by direct halogenation. A superior method of halogenation of teraalkyl methylenediphosphonates is also described. The reaction of metalated tetraalkyl methylenediphosphonate with molecular oxygen in toluene solution is shown to be complex.

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