caa a22 4500 467990581 CHVBK 20180323112543.0 cr unu---uuuuu 170328e19900101xx s 000 0 eng 10.1007/BF00506848 doi (NATIONALLICENCE)springer-10.1007/BF00506848 Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines [Elektronische Daten] [G. Litvinenko, E. Yalovenko] The 13C NMR spectra of 5-keto- and 5a- and 5e-hydroxy-10-methyl- and 1,10-dimethyltrans-decahydroquinolines have been recorded and interpreted. The increments of the oxo and hydroxy groups in the 10-methyldecahydroquinoline and the isostructural 10-methyldecaline systems were compared. The difference between the increments of azacyclic and the carbocyclic systems appears- at the γ-positions relative to the electronegative substituents (C(7) and C(9)) and at the antiperiplanar γ-positions relative to nitrogen (C(5) and C(7)). The increments of the oxo and the equatorial hydroxy groups in the aza ring are more shielded than in the carbon ring (at C(7), 2 ppm; at C(g), 1 ppm), while the increments of the axial hydroxy group are more deshielded (at C(5), 1.5-2.0 ppm; at C(9), 1.0-1.5 ppm). The more the respective carbon atoms of the heterocycle are hydrogenated, the stronger are the deshielding Β-effect and the shielding γ-effect of the methyl group on nitrogen. Plenum Publishing Corporation, 1990 Litvinenko G. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSR, 480100, Alma-Ata aut Yalovenko E. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSR, 480100, Alma-Ata aut Chemistry of Heterocyclic Compounds Kluwer Academic Publishers-Plenum Publishers 26/1(1990-01-01), 53-57 0009-3122 26:1<53 1990 26 10593 https://doi.org/10.1007/BF00506848 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00506848 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Litvinenko G. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSR, 480100, Alma-Ata aut NATIONALLICENCE 700 1- Yalovenko E. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSR, 480100, Alma-Ata aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Kluwer Academic Publishers-Plenum Publishers 26/1(1990-01-01), 53-57 0009-3122 26:1<53 1990 26 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer