1H n.m.r. spectra of some bicyclic compounds: I—relative configurations of the diastereomeric endo-α-methyl-5-norbornene-2-methanols,the corresponding saturated analogues,and their cyclization ether products |
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| Authors: | M Lj Mihailovi&#x; S Milosavljevi&#x; D Jeremi&#x; J Milovanovi&#x; |
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| Institution: | M. Lj. Mihailović,S. Milosavljević,D. Jeremić,J. Milovanović |
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| Abstract: | The configurational and conformational relationship at C-2 and C-α in the two racemic diastereomeric endo-α-methyl-5-norbornene-2-methanols and the corresponding saturated endo-α-methyl-2-norbornanemethanols were determined by first-order analysis of the 1H n.m.r. spectra of these compounds and of their cyclization ether products, i.e. 3-methyl-2-oxatricyclo4.2.1.04,8]nonanes and 5-methyl-4-oxatricyclo4.3.0.03,8]nonanes. In addition, the conformational preference of the hydroxyl group in the unsaturated and saturated alcohols was confirmed by the lanthanide induced shift technique, using Eu(fod)3 as shift reagent, combined with a computer program involving various conformations of the –CHOHMe group. |
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