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NMR spectroscopic characterization of ZE isomers of cyclododeca-1,5,9-triene

✍ Scribed by Reiner Radeglia; Helmut Poleschner; GÜNter Haufe


Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
228 KB
Volume
31
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

The four Z____E isomers of cyclododeca‐1,5,9‐triene were examined by ^13^C NMR spectroscopy. The vicinal ^1^H^1^H coupling constants of the olefinic protons were used to determine the stereochemistry at the double bonds. For the symmetrically substituted CHCH fragments (chemically equivalent H atoms) this parameter was obtained from the ^13^C NMR multiplets which are observed in ^1^H continuous‐wave off‐resonance ^13^C NMR experiments. The precise assignment of the ^1^H and ^13^C chemical shifts, in particular for the Z,Z,E and Z,E,E isomers, was possible on the basis of off‐resonance measurements in combination with ^13^C/^1^H heteronuclear correlated and ^1^H/^1^H‐COSY‐45 2D experiments.


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