3,4-Unsubstituted 2-<i>tert</i>-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains

Abstract

Pyrrolidine nitroxides with four bulky alkyl substituents adjacent to N–O group are known for their high resistance to bioreduction. The 3,4-unsubstituted 2-tert-butyl-2-ethylpyrrolidine-1-oxyls were prepared from the corresponding 2-tert-butyl-1-pyrroline-1-oxides via either the addition of ethinylmagnesium bromide with subsequent hydrogenation or via treatment with ethyllithium. The new nitroxides showed excellent stability to reduction with ascorbate with no evidence for additional large hyperfine couplings in the EPR spectra.

Keywords

• nitroxides
• nitrones
• organometallic compounds
• pyrrolidine
• reduction kinetics