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Conformational isomerism of 2‐carboazetidines
Author(s) -
Rodebaugh Richard M.,
Cromwell Norman H.
Publication year - 1971
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570080312
Subject(s) - chemistry , conformational isomerism , steric effects , epimer , dipole , alkyl , infrared spectroscopy , infrared , computational chemistry , spectral line , stereochemistry , organic chemistry , molecule , physics , astronomy , optics
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.