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Proton magnetic resonance studies of compounds with bridgehead nitrogen atoms—XXIV: The stereochemistry of octahydroimidazo [1,5‐ a ] pyridine and of some N ‐acetyloctahydroimidazo [1,5‐ a ] pyridines
Author(s) -
Crabb T. A.,
Chivers P. J.,
Newton R. F.
Publication year - 1973
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270050810
Subject(s) - pyridine , chemistry , proton magnetic resonance , ring (chemistry) , pyrimidine , nitrogen , crystallography , proton , stereochemistry , cis–trans isomerism , resonance (particle physics) , spectral line , nuclear magnetic resonance , medicinal chemistry , organic chemistry , physics , quantum mechanics , astronomy , particle physics
Octahydroimidazo[1,5‐ a ]pyridine is shown to preferentially adopt the trans ‐fused ring conformation in solution at room temperature. The NMR spectra of the rotational isomers of some N ‐acetyloctahydroimidazo[1,5‐ a ]pyridines and N ‐acetyloctahydro‐1H‐pyrido[1,2‐ c ]pyrimidine are described, and the stereochemistry about the N ‐acetyl bonds and the cis or trans nature of the ring fusion defined.