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1 H 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
Author(s) -
Mihailović M. Lj.,
Milosavljević S.,
Jeremić D.,
Milovanović J.
Publication year - 1977
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270090411
Subject(s) - diastereomer , norbornene , chemistry , reagent , bicyclic molecule , ether , stereochemistry , nmr spectra database , spectral line , lanthanide , methyl group , group (periodic table) , organic chemistry , ion , physics , monomer , astronomy , polymer
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.