Base Catalyzed Reactions with RX, CH2O, Olefins and R2NCH2OH

Base Catalyzed Reactions with RX, CH2O, Olefins and R2NCH2OH 

Reaction of wliite phosphorus with sodium hydroxide or sodium etlioxide in ethanol generates a dark red solution of an uncharacterized metastable phosphorus compound which possesses nucleopliilic properties The red product decomposes slowly even at 0 °C to hydrogen, PH3 and sodium hypophosphite 

But addition of methyl iodide to the solution gives CH3PH2, CH3PO3H2, (CH3)2PO2H and (CH3)3PO Analogous products were reported from reactions of iso-amyl iodide. 

Organic phosphorus compounds are also produced in the interaction of wliite phosphorus with an epoxide or an episulfide and an alcohol or mercaptane in the presence of alkaline catalysts at 25 °C to 200 °C In order to remove P-H bonds the reaction mixture is treated witli formaldehyde and oxidized. The products are said to be useful as hardeners for epoxy resins or as antistatic agents and fire retardants. 

High yields of bis (hydroxymethyl) phosphinic acid ( 90%) have been claimed to be formed in the reaction of white phosphorus with formaldehyde in a basic alcohol/ water medium at 45-65 °C. Other aldehydes apparently react similarly  

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