Conclusions
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1.
Z, E Configurations of unsaturated azlactones and their solvolysis products were established by means of the vicinal spin-spin coupling constant, J13C,H, determined in the13C NMR spectra. Previously published assumptions of a uniform olefin-bond configuration in unsaturated azlactones and their solvolysis products were confirmed.
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2.
Z and E isomers were identified by the number of signals in the 135–151 ppm region of the13C NMR spectrum.
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3.
The chemical shift values of the Hβ proton are characteristic of Z,E isomers of unsaturated azlactones.
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4.
Conjugation of the olefin and carbonyl bonds is assumed to be more effective in the E isomers of azlactones than in the Z isomers.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 823–829, April, 1980.
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Prokof'ev, E.P., Karpeiskaya, E.I., Chel'tsova, G.V. et al. Direct determination of Z, E configuration of 4-arylidene-2-phenyl(methyl)-δ2-oxazolin-5-ones and their solvolysis products by13c NMR. Russ Chem Bull 29, 576–582 (1980). https://doi.org/10.1007/BF00961606
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DOI: https://doi.org/10.1007/BF00961606