Phosphoric amides. Part 8. The effect of the ethylenimine substituent on the solvolytic reactivity of phosphate and phosphoramidate bonds

Abstract

Rates and products of the base-catalysed hydrolysis of some amidoesters of phosphoric acid have been determined. In the N,N-dimethyl derivative, the P–N bond is resistant, and the P–O bond deactivated towards hydrolysis, while in the N-methyl substrate, the reactivity of the ester link is similar to that in trimethyl phosphate. In the N-ethylene compound, both P–O and P–N bonds are strongly activated. The N-(β-chloroethyl) substrate reacts via fast, base-catalysed cyclization to the N-ethylene amidate.