Phosphite ester

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A phosphite ester or organophosphite is a type of chemical compound with the general structure P(OR)₃. Phosphite esters can be considered as esters of phosphorous acid, H₃PO₃. A simple phosphite ester is trimethylphosphite, P(OCH₃)₃. Phosphite esters can be prepared by reacting phosphorus trichloride or phosphorus tribromide with an alcohol and a tertiary amine.

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^[1] (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.

The compound trimethylolpropane phosphite is a ligand used in organometallic chemistry.

See also

• Organophosphorus chemistry

References

1. ^ J. N. Gardner, F. E. Carlon and O. Gnoj (1968). "One-step procedure for the preparation of tertiary α-ketols from the corresponding ketones". J. Org. Chem. 33 (8): 3294-3297. doi:10.1021/jo01272a055.