Nucleophilic Reactivity of N-Phosphorylated Ethyleneimine†

Abstract

The diesters of N-phosphorylated ethyleneimine (aziridine) are unreactive towards alkylating agents, but after being converted into the ionic monoesters, they undergo facile N-methylation with MeI, followed by fast opening at the aziridinium ring by the iodide ion; the results can be related to the bis-alkylating reactivity of N-phosphorylated nitrogen mustards.