Synthesis of N-Alkoxyamines from Nitroxide Radicals and Aldehydes

Significance

A novel expedient method for the synthesis of 2,2,6,6-tetramethylpiperidine-based N-alkoxyamines has been disclosed. In this reaction aldehydes act as a superb source for alkyl radical species, avoiding selectivity problems which may occur with ketones as radical sources. This method was found to tolerate a broad variety of functional groups which are usually subject to radical reactions, such as C=C bonds, nitro, ­cyano and alcohol functionalities.