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Nuclear magnetic resonace spectra of substituted oxazoles and oxazolidinones
Author(s) -
Deavenport Dennis L.,
Harrison C. H.,
Rathburn D. W.
Publication year - 1973
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.1270050608
Subject(s) - ring (chemistry) , oxazole , chemistry , chemical shift , spectral line , range (aeronautics) , coupling (piping) , stereochemistry , materials science , physics , organic chemistry , quantum mechanics , metallurgy , composite material
During the synthesis of 2,5‐disubstituted oxazoles and 4‐oxazolidinones, NMR spectroscopy was utilized to obtain information on the structure, bonding and geometric isomerism in the various compounds. Long range couplings between substituents attached at C 2 and C 5 in both ring systems was of particular utility in this respect. The aromaticity of the oxazole ring is substantiated by the ability of the π system to transmit long range coupling through the ring and by the chemical shifts of the ring protons. Geometric isomers of the 4‐oxazolidinones are identified by observing long‐range cis and trans couplings of the order of 1·8 to 2·4 Hz.