Relative nucleophilic reactivity of pyridines and pyridine N-oxides (supernucleophilicity of pyridine N-oxides)

Supernucleophilicity of pyridine N-oxides in acyl transfer reactions was rationalized for the first time on a theoretical level. Unlike pyridines, transition state derived from pyridine N-oxides is stabilized by direct conjugation between the nucleophilic and electrophilic components.