1H n.m.r. long-range coupling in 2,4-disubstituted-5(4H)-oxazolones and 4-alkyl-5(2H)-oxazolones generated therefrom by the action of triethylamine.
Long-range couplings were observed between H-4 and 2-CCHn of 2,4-disubstituted-5(4H)-oxazolones, and H-4 and H-2 of 4-alkyl-5(4H)-oxazolones. In the presence of triethylamine, H-4 of the latter migrates to C-2 accompanied by a shift of the double bond to give 4-alkyl-5(2H)-oxazolones which show 5J coupling between H2-2 and 4-CCHn protons.
Department of Biochemistry, University of Ottawa, Ontario, Canada.
F M
FM
Chen
N L
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Benoiton
D005021:Ethylamines; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles; D010081:Oxazolone / Q000031:analogs & derivatives*; D010455:Peptides / Q000138:chemical synthesis*
D005021:Ethylamines; D010080:Oxazoles; D010455:Peptides; D010081:Oxazolone; C016162:triethylamine