EXPERIMENTAL TESTS OF THE STEREOELECTRONIC EFFECT AT PHOSPHORUS: MICHAELIS-ARBUSOV REACTIVITY OF PHOSPHITE ESTERS.

Article abstract of DOI:10.1016/0040-4020(84)85003-6

Whereas triethyl phosphite readily reacts with benzoyl chloride to yield the Michaelis-Arbusov product, diethyl benzoyl phosphonate, 1-methyl-4-phospha-3,5,8-trioxabicyclo<2.2.2>octane, 1, is essentially unreactive, even at a higher temperature.The bicyclic phosphite 1 also reacts slower than the triethyl phosphite 2 in an oxidation with t-butyl hydroperoxide.These results are interpreted in terms of the stereoelectronic effect.