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
✍ Scribed by M. Lj. Mihailović; S. Milosavljević; D. Jeremić; J. Milovanović
- Publisher
- John Wiley and Sons
- Year
- 1977
- Tongue
- English
- Weight
- 553 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0749-1581
No coin nor oath required. For personal study only.
✦ Synopsis
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 ^1^H n.m.r. spectra of these compounds and of their cyclization ether products, i.e. 3‐methyl‐2‐oxatricyclo[4.2.1.0^4,8^]nonanes and 5‐methyl‐4‐oxatricyclo[4.3.0.0^3,8^]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.