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The synthesis and spectra of new ( E )‐( trans ) and ( Z )‐( cis )‐1‐alkyl‐2‐aryl (alkyl) ‐ 3 ‐aroylaziridines
Author(s) -
Tarburton Philip,
Wolpa Lori J.,
Loerch Robert K.,
Folsom Thomas L.,
Cromwell Norman H.
Publication year - 1977
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.5570140715
Subject(s) - chemistry , alkyl , conformational isomerism , aryl , amine gas treating , primary (astronomy) , medicinal chemistry , stereochemistry , organic chemistry , molecule , physics , astronomy
The synthetic scope of the reaction of primary amines with α,β‐dibromochalones to form aroylaziridines is explored and found to require at least one hydrogen on the α‐carbon of the amine. Fourteen new epimeric l‐alkyl‐2‐aryl(alkyl)‐3‐aroylaziridines are synthesized accordingly. Next, representative aroylaziridines are investigated by infra‐red spectroscopy in solvents of ambient polarity to assess the relative populations of the gauche and cisoid conformers present in the ( Z )‐( cis ) series.