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Configuration and conformation of some 4‐hydroxy‐ cis ‐ and ‐ trans ‐1‐oxadecalins
Author(s) -
Dolmazon René,
Gelin Suzanne
Publication year - 1985
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260231103
Subject(s) - chemistry , steric effects , ring (chemistry) , substituent , diastereomer , tetrahydropyran , stereochemistry , nuclear magnetic resonance spectroscopy , oxygen atom , cis–trans isomerism , carbon 13 nmr satellite , nmr spectra database , crystallography , spectral line , fluorine 19 nmr , molecule , organic chemistry , physics , astronomy
The configuration and conformation of some diastereomeric 4‐hydroxy‐ cis ‐ and ‐ trans ‐1‐oxadecalins were inferred by 1 H and 13 C NMR spectroscopy. The results obtained indicate that the cis ‐fused compounds are conformationally homogeneous, having the oxygen atom attached to the cyclohexyl ring in the axial position. In the 13 C NMR spectra, the magnitude of the α and γ substituent effects of the hydroxy group is rationalized in terms of steric deformations of the tetrahydropyran ring.