Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines
Abstract 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...
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E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1990 |
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5 |
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| Reproduktion: |
Springer Online Journal Archives 1860-2002 |
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| Übergeordnetes Werk: |
in: Chemistry of heterocyclic compounds - 1965, 26(1990) vom: Jan., Seite 53-57 |
| Übergeordnetes Werk: |
volume:26 ; year:1990 ; month:01 ; pages:53-57 ; extent:5 |
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| 245 | 1 | 0 | |a Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines |
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| 520 | |a Abstract 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. | ||
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(DE-627)NLEJ190408308 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines 1990 5 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract 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. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Yalovenko, E. G. oth in Chemistry of heterocyclic compounds 1965 26(1990) vom: Jan., Seite 53-57 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:26 year:1990 month:01 pages:53-57 extent:5 http://dx.doi.org/10.1007/BF00506848 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 26 1990 1 53-57 5 |
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(DE-627)NLEJ190408308 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines 1990 5 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract 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. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Yalovenko, E. G. oth in Chemistry of heterocyclic compounds 1965 26(1990) vom: Jan., Seite 53-57 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:26 year:1990 month:01 pages:53-57 extent:5 http://dx.doi.org/10.1007/BF00506848 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 26 1990 1 53-57 5 |
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(DE-627)NLEJ190408308 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines 1990 5 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract 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. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Yalovenko, E. G. oth in Chemistry of heterocyclic compounds 1965 26(1990) vom: Jan., Seite 53-57 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:26 year:1990 month:01 pages:53-57 extent:5 http://dx.doi.org/10.1007/BF00506848 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 26 1990 1 53-57 5 |
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(DE-627)NLEJ190408308 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines 1990 5 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract 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. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Yalovenko, E. G. oth in Chemistry of heterocyclic compounds 1965 26(1990) vom: Jan., Seite 53-57 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:26 year:1990 month:01 pages:53-57 extent:5 http://dx.doi.org/10.1007/BF00506848 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 26 1990 1 53-57 5 |
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(DE-627)NLEJ190408308 DE-627 ger DE-627 rakwb eng Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines 1990 5 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Abstract 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. Springer Online Journal Archives 1860-2002 Litvinenko, G. S. oth Yalovenko, E. G. oth in Chemistry of heterocyclic compounds 1965 26(1990) vom: Jan., Seite 53-57 (DE-627)NLEJ188993940 (DE-600)2037128-7 1573-8353 nnns volume:26 year:1990 month:01 pages:53-57 extent:5 http://dx.doi.org/10.1007/BF00506848 GBV_USEFLAG_U ZDB-1-SOJ GBV_NL_ARTICLE AR 26 1990 1 53-57 5 |
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stereochemistry of nitrogen heterocycles. 69. 13c nmr spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines |
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Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines |
| abstract |
Abstract 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. |
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Abstract 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. |
| abstract_unstemmed |
Abstract 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. |
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<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">NLEJ190408308</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230506100630.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">070525s1990 xx |||||o 00| ||eng c</controlfield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)NLEJ190408308</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Stereochemistry of nitrogen heterocycles. 69. 13C NMR spectra of stereoisomeric 10-methyl-5-oxygen-substituted trans-decahydroquinolines</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">1990</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">5</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">z</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zu</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract 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.</subfield></datafield><datafield tag="533" ind1=" " ind2=" "><subfield code="f">Springer Online Journal Archives 1860-2002</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Litvinenko, G. S.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Yalovenko, E. G.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">in</subfield><subfield code="t">Chemistry of heterocyclic compounds</subfield><subfield code="d">1965</subfield><subfield code="g">26(1990) vom: Jan., Seite 53-57</subfield><subfield code="w">(DE-627)NLEJ188993940</subfield><subfield code="w">(DE-600)2037128-7</subfield><subfield code="x">1573-8353</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:26</subfield><subfield code="g">year:1990</subfield><subfield code="g">month:01</subfield><subfield code="g">pages:53-57</subfield><subfield code="g">extent:5</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">http://dx.doi.org/10.1007/BF00506848</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">ZDB-1-SOJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_NL_ARTICLE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">26</subfield><subfield code="j">1990</subfield><subfield code="c">1</subfield><subfield code="h">53-57</subfield><subfield code="g">5</subfield></datafield></record></collection>
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