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Aryloxydihydropyrans. XII. Configuration and conformations of 8-(3,4-dihydro-2-pyranyloxy)quinoline derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The configuration and conformations of stereoisomeric 4R-8-(3,4-dihydro-2-pyranyloxy)quinolines were studied by means of their PMR spectra. It was established that the trans isomers of the investigated compounds have primarily a “half-chair” conformation and display an anomeric effect. A “sofa” conformation is proposed for the labile cis isomers.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 607–610, May, 1976.

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Sigalov, M.V., Voronov, V.K., Andriyankov, M.A. et al. Aryloxydihydropyrans. XII. Configuration and conformations of 8-(3,4-dihydro-2-pyranyloxy)quinoline derivatives. Chem Heterocycl Compd 12, 508–511 (1976). https://doi.org/10.1007/BF00470100

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  • DOI: https://doi.org/10.1007/BF00470100

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