Phosphite ester

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A phosphite ester is a type of chemical compound with the general structure P(OR)3 and derived from phosphites. A simple phosphite ester is trimethylphosphite P(OCH3)3. They are 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.

Scheme 1. Autoxidation of a keto steroid with oxygen to the hydroperoxide (not depicted) followed by reduction with triethylphosphite to the alcohol

This reaction type is also utilized in the Wender Taxol total synthesis.

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[edit] References

  • ↑  One-step procedure for the preparation of tertiary .alpha.-ketols from the corresponding ketones J. N. Gardner, F. E. Carlon, O. Gnoj J. Org. Chem.; 1968; 33(8); 3294-3297. Abstract
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