Investigation into the Chemistry of Highly Substituted [(Aminocyclopropyl)methyl]alkoxyamines (3-Azabicyclo[3.1.0]hexanes)

Enamines prepared from N-alkoxy-4-oxo-2,2,6,6-tetramethylpiperidines were selectively chlorinated in the allyl position and subsequently transformed into bicyclic [(aminocyclopropyl)methyl]alkoxyamines by reaction with various nucleophiles. The products were formed, supposedly via iminium intermediates, in reasonable to high yields, possessing varying degrees of hydrolytic stability. Structural elucidation by NMR spectroscopy strongly suggested an endo position of the amine substituent. The obtained, highly functionalized alkoxyamines could be of interest as polymer additives or biologically active intermediates.