Synthesis of bifunctionalized nitroxyls via intramolecular epoxide ring opening

The syntheses of nitroxyl oxirane and further functionalized derivatives are described. Ring-cleavage reactions of this epoxide have been carried out with a variety of nucleophiles in order to show the general synthetic utility for preparing nitroxyls bearing two functional groups. The relatively facile synthesis of the nitroxyl amino alcohol should prove to be valuable in various spin labeling applications.