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 | Zendy

Mihailović M. Lj. | Zendy; Milosavljević S. | Zendy; Jeremić D. | Zendy; Milovanović J. | Zendy

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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.

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