Reaction of Azetidines with Chloroformates

The reaction of an azetidine with a chloroformate can give either the dealkylated heterocycle or the ring-opened product (γ-chloroamine), which can further cyclize to the oxazinanone. A general study of this underrated reaction was conducted and revealed that azetidines can undergo smooth nucleophilic ring-opening reactions to highly functionalized γ-chloroamines in the presence of a variety of alkyl chloroformates under mild reaction conditions. Yields are usually good, and parameters governing this reaction were evaluated.