Regioselective Nucleophilic Opening of Azetidinium Ions

Azetidinium ions bearing different substitution patterns were reacted with nitrogen nucleophiles (sodium azide and benzylamine) and oxygenated nucleophiles (sodium acetate and alkoxides). High regioselectivity of nucleophilic opening was observed in both cases: the nucleophile reacting on the unsubstituted carbon in the case of (alpha)-substituted azetidinium salts and on the carbon bearing an ester or cyano moiety in the case of (alpha),(alpha)’-substituted azetidinium salts.