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Nuclear magnetic resonance spectra of codeine and isocodeine derivatives

✍ Scribed by Arthur E. Jacobson; Herman J. C. Yeh; Lewis J. Sargent

Publisher
John Wiley and Sons
Year
1972
Tongue
English
Weight
388 KB
Volume
4
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The NMR spectra of a spiro oxirane (1) derivative of codeinone, codeine (2), isocodeine (3), 6‐methylcodeine (4) and 6‐methylisocodeine (5) were compared. NOE and double‐resonance experiments were used to confirm the conformation of 1, and the configuration about C‐6 of 6‐methylcodeine and 6‐methylisocodeine. An interchange of the chemical shifts of the olefinic protons in 1 was noted, as compared with those in all of the other compounds. This interchange could be attributed to the bond anisotropies of the oxirane moiety.

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