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

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‐oxatricyclo[4.2.1.04,8]nonanes and 5‐methyl‐4‐oxatricyclo[4.3.0.03,8]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.