Conformational isomerism of 2‐carboazetidines

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Abstract
A number of 1‐alkyl‐2‐carboazetidines have been prepared from the reaction of primary amines with α,γ‐dibromocarbonyl compounds. Several of these new azetidines exhibit doublet carbonyl stretching absorptions in their infrared spectra. A possible explanation of this phenomenon is offered in terms of three rotational conformers which represent various degrees of dipole‐dipole and steric interactions. The cis and trans forms of 1‐t‐butyl‐2‐carbomethoxy‐4‐methylazetidine have been obtained from the reaction of t‐butylamine with methyl α,γ‐dibromovalerate. A detailed examination indicates that the ir and nmr spectra of these epimers are in agreement with the foregoing conformational postulates.