Abstract
The1H and13C NMR spectra of the diastereomers of 3-phenyl-5-isopropoxytetrahydro-2-furanone were obtained. The stereoisomerism and preferred conformational states of these diastereomers were established by means of the spectroscopic criteria found for 3,4-disubstituted sulfolanes and 1,1,3,4-tetrasubstituted silacyclopentanes. It is shown that for the cis isomer the equilibrium is shifted to favor pseudoequatorial conformers, whereas for the trans isomer it shifted to favor ae conformers with a preferred pseudoequatorial orientation of phenyl substituent.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 593–597, May, 1988.
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Panasenko, A.A., Fatykhov, A.A., Spirikhin, L.V. et al. 1H and13C NMR spectra, stereoisomerism, and conformational states of 3-phenyl-5-isopropoxytetrahydro-2-furanones. Chem Heterocycl Compd 24, 480–484 (1988). https://doi.org/10.1007/BF00755684
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DOI: https://doi.org/10.1007/BF00755684