Modified polonovski reactions in ionic liquid solvents

Abstract

A modified Polonovski reaction using an iron (0) catalyst has been shown to be an effective means of N-demethylating opiate and pseudo-opiate compounds.1 It has also been demonstrated that the choice of solvent in this reaction is of major significance as solvent effects play a large role in yields of N-demethylated product; isolated yields ranged from 59% (methanol) to 97% (chloroform). The current work aims to utilize the highly polar yet non-coordinating properties of ionic liquids as a reaction solvent. Ionic liquid solvents possess the added benefit of maximizing the solubility of the N-oxide hydrochloride starting material necessary for the modified Polonovski reaction. Use of commercial magnetite and rust nanoparticles as catalysts in ionic liquids for the modified Polonovski reaction will be discussed.