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A 1H and 13C NMR study of methoxyretinoids. Spectral assignment and determination of configuration

✍ Scribed by Ludger Ernst; Henning Hopf; Konstantin Natsias

Publisher
John Wiley and Sons
Year
1984
Tongue
English
Weight
487 KB
Volume
22
Category
Article
ISSN
0749-1581

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✦ Synopsis

A number of modified retinals and retinoic esters carrying one or two methoxy groups or one methoxy and one methyl group on the polyene chain were investigated by 'H and " C NMR spectroscopy. Spectral assignments were made from homo-and selective =C{'H} hetero-decoupling experiments and from chemical shift comparisons. The configurations of the polyene double bonds were derived fmm vicinal H,H coupling constants, from 'H and -C chemical shifts and by measuring nuclear Overhauser enhancements. It is found that aU double bonds with no additional substituents occur in the trans ( E ) and all methoxy-substituted double bonds in the cis (also E) confignration. Double bonds carrying methyl groups give rise to both cis (Z) and trans ( E ) isomers.

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