Facile ring cleavage of basic azetidines

Azetidines containing a basic ring nitrogen atom have been shown to undergo facile ring cleavage to afford 3-halo-1-amino propane derivatives upon exposure to alkyl bromides and acyl chlorides under certain conditions. Alkylation of NH azetidines to afford N-alkyl azetidines can be carried out in synthetically useful yields if reaction times are kept short. As the free base, azetidines may undergo spontaneous oligomerization with concomitant ring cleavage.