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Studies in the synthesis of C‐ring bridged morphinans 3 — 13 C NMR analysis of some simple and complex bicyclooctane derivatives
Author(s) -
Roche Victoria F.,
Nagel Donald L.,
Roche Edward B.
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.1260230916
Subject(s) - chemistry , chemical shift , heteroatom , protonation , carbon 13 nmr , molecule , ring (chemistry) , octane , bicyclic molecule , computational chemistry , stereochemistry , nmr spectra database , nuclear magnetic resonance spectroscopy , proton nmr , spectral line , organic chemistry , ion , physics , astronomy
The 13 C NMR spectra of eight novel derivatives of bicyclo[2.2.2]‐ and ‐[3.2.1]octane have been recorded and analysed. These compounds were isolated and characterized as intermediates in the synthesis of a unique derivative of 1,2,3,3a,11b,11c‐hexahydroaporphine. Carbon chemical shift assignments of the molecules under investigation were based on 13 C NMR theory including splitting patterns, differences in chemical shift values of carbons α and β to amino nitrogens in their protonated and non‐protonated forms, and through the anticipated shielding effects of γ‐ syn and γ‐ anti heteroatoms. This latter method of analysis was particularly useful in assigning the chemical shift values of carbons in the bicyclooctane region of the simpler molecules.