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Analysis of 1H and 13C NMR spectra of cis- and trans-10-substituted decal-2-ones by 2D NMR techniques

✍ Scribed by G. Di Maio; L. M. Migneco; E. Vecchi; C. Iavarone

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
86 KB
Volume
38
Category
Article
ISSN
0749-1581

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✦ Synopsis

The 1 H and 13 C NMR chemical shift assignments of 10-substituted decal-2-ones, cis (H, CH 3 and CO 2 CH 3 ) and trans (H, CH 3 , OH and CO 2 C 2 H 5 ) were based on 2D COSY and HETCOR experiments, supported by selective spin decoupling experiments. The discrimination between the cis and the trans conformations was ruled out on the basis of the J(1a,9) magnitudes related to dihedral angles (Karplus rule) and also on the 13 C shielding values of C-4 of the cis compounds, which are much more shielded than those of the trans counterparts. The best and fastest criterion of differentiation between cis and trans conformers is the constant appearance in the 13 C PND spectra of the cis series of some signals of broadened linewidth and low intensity, essentially C-4, C-5 and C-7, a clue to site exchange processes; the trans counterparts showed only sharp signals because of their existence as a single conformation.

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