Stereochemical effects in the reactions of n-alkyl-4-substituted azetidine 2-carboxylic acids with oxalyl chloride. Rearrangement to chloro-γ-lactams.

Treatment of N-alkylazetidine 2-carboxylates with oxalyl chloride may yield acid chlorides, iminium salts or chloro-γ-lactams depending on the stereochemistry and nature of the substituents on the azetidine ring.