The phosphoryl cation as an intermediate in the reaction of benzoyl phosphates

Abstract

By means of a system of geometrical isomers, cis- and trans-2-benzoyloxy-5-chloromethyl-5-methyl-2-oxo-1,3,2-dioxaphosphorinans, evidence is presented which strongly suggests that benzoyl phosphate esters may ionize to phosphoryl cations. The degree of ionization which can be followed by observing a change in the isomer ratio is solvent dependent with ion pairs formed in solvents of moderate polarity. Based on the known equilibration of benzoyl phosphates to pyrophosphate, solvent-separated ions are pictured as being formed in solvents of high polarity.