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NMR Spectra and Stereochemistry of some 7‐Substituted 6,14‐Bridged Thebaine Derivatives
Author(s) -
Uff Barrie C.,
Mallard Angela S.,
Davis John A.,
Henson Ray
Publication year - 1985
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260230610
Subject(s) - thebaine , chemistry , steric effects , substituent , stereochemistry , spectral line , nmr spectra database , proton nmr , proton , series (stratigraphy) , computational chemistry , astronomy , pharmacology , paleontology , quantum mechanics , biology , medicine , physics , codeine , morphine
The NMR spectra of eighteen 7α‐ and 7β‐substituted 6,14‐bridged thebaine derivatives are reported and the steric and other effects of the 7‐substituent on the C‐5‐H atoms examined. Although the H‐5 proton shift enabled compounds epimeric at C‐7 to be distinguished in the examples studied (values falling between δ 4.75‐4.40 ppm in the 7α series and δ 5.21‐4.97 ppm in the 7β series), the C‐5 shift values proved less useful owing to overlapping ranges.