Phosphite ester
In chemistry a phosphite ester or organophosphite is a type of organophosphorous compound with the general structure P(OR)3. They can be considered as esters of phosphorous acid, H3PO3, with the simplest example being trimethylphosphite, P(OCH3)3.
Phosphite esters can be prepared by reacting phosphorus trichloride or phosphorus tribromide with an alcohol. The reaction can be catalysed by the presence of a suitable non-nucleophic base, such as a tertiary amine, which will remove the HCl or HBr by-product.
Phosphite esters adopt trigonal pyramidal molecular geometry due to the lone pairs on the phosphorous. As such they typically display C3vmolecular symmetry.
Phosphite esters are used in the Perkow reaction in the formation of vinyl phosphonates and in the Michaelis–Arbuzov reaction to form phosphonates. One other particular use is that of reducing agent. For example, triethylphosphite is known to reduce certain hydroperoxides to alcohols formed by autoxidation (scheme 1). In this process the phosphite is converted to a phosphate ester.
This reaction type is also utilized in the Wender Taxol total synthesis.
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