Nucleophilic reactivity of organophosphorus compounds. Part 3. Kinetics and mechanism of the reaction of phosphorus acids with keten OO-acetals in aprotic medium

Abstract

The kinetics of the reactions of OO-diethyl S-hydrogen phosphorodithioate and O-ethyl S-hydrogen methylphosphonodithioate with p-nitrophenylketen dialkyl acetals in di-n-butyl ether as solvent are reported and discussed in terms of a mechanism which involves a highly reversible protonation (probably to an ion-pair) followed by nucleophilic attack by the phosphorus anion on the intermediate carbonium ion of the ion-pair.