Experimental tests of the stereoelectkoic effect at phosphoru: Michaelis-Arbusov reactivity of phosphite esters

Whereas triethyl phosphite readily reacts with benzoyl chloride to yield the Michaelis-Arbusov product, diethyl benzoyl phosphonate, 1-methyl-4-phospha-3,5,8-trioxabi)cyclo2.2.2]octane, $\text{1}$, is essentially unreactive, even at a higher temperature. The bicyclic phosphite $\text{1}$ also reacts slower than the triethyl phosphite $\text{2}$ In an oxidation with t-butyl hydroperoxide. These results are interpreted in terms of the stereoelectronic effect.