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Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines
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| Zeitschriftentitel: | European Journal of Organic Chemistry |
|---|---|
| Personen und Körperschaften: | , , |
| In: | European Journal of Organic Chemistry, 2006, 2006, 20, S. 4664-4669 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Tóth, Diána Szatmári, István Fülöp, Ferenc Tóth, Diána Szatmári, István Fülöp, Ferenc |
|---|---|
| author |
Tóth, Diána Szatmári, István Fülöp, Ferenc |
| spellingShingle |
Tóth, Diána Szatmári, István Fülöp, Ferenc European Journal of Organic Chemistry Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines Organic Chemistry Physical and Theoretical Chemistry |
| author_sort |
tóth, diána |
| spelling |
Tóth, Diána Szatmári, István Fülöp, Ferenc 1434-193X 1099-0690 Wiley Organic Chemistry Physical and Theoretical Chemistry http://dx.doi.org/10.1002/ejoc.200600447 <jats:title>Abstract</jats:title><jats:p>New 1‐(1‐aminoalkyl)‐2‐naphthols <jats:bold>8</jats:bold>–<jats:bold>11</jats:bold> have been synthesised by the condensation of 2‐naphthol with aliphaticaldehydes in the presence of ammonia, followed by acidic hydrolysis. The condensation of <jats:bold>7</jats:bold>–<jats:bold>11</jats:bold> with substitutedbenzaldehydes after microwave irradiation led to1‐alkyl‐3‐aryl‐2,3‐dihydro‐1<jats:italic>H</jats:italic>‐naphth[1,2‐<jats:italic>e</jats:italic>][1,3]oxazines,which proved to be three‐component (r<jats:sup><jats:italic>t</jats:italic></jats:sup>‐o‐r<jats:sup><jats:italic>c</jats:italic></jats:sup>) tautomeric mixtures in CDCl<jats:sub>3</jats:sub> at 300 K. The electronic effects of the 1‐alkyl and 3‐aryl groups on the tautomeric ratios could be determined for both the ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and the ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria with the aid of two‐variant linear equations. A significant difference was found between the coefficients of the Meyer parameter <jats:italic>V</jats:italic><jats:sup>a</jats:sup>, which characterises the volume of the portion of the alkyl substituent within 0.3 nm of the reaction centre, for ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria, and this is explained in terms of the stereoelectronic effect caused by the alkyl substituent at position 1. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)</jats:p> Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐<i>e</i>][1,3]oxazines European Journal of Organic Chemistry |
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Wiley, 2006 |
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| title |
Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_unstemmed |
Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_full |
Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_fullStr |
Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_full_unstemmed |
Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_short |
Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_sort |
substituent effects in the ring–chain tautomerism of 1‐alkyl‐3‐arylnaphth[1,2‐<i>e</i>][1,3]oxazines |
| topic |
Organic Chemistry Physical and Theoretical Chemistry |
| url |
http://dx.doi.org/10.1002/ejoc.200600447 |
| publishDate |
2006 |
| physical |
4664-4669 |
| description |
<jats:title>Abstract</jats:title><jats:p>New 1‐(1‐aminoalkyl)‐2‐naphthols <jats:bold>8</jats:bold>–<jats:bold>11</jats:bold> have been synthesised by the condensation of 2‐naphthol with aliphaticaldehydes in the presence of ammonia, followed by acidic hydrolysis. The condensation of <jats:bold>7</jats:bold>–<jats:bold>11</jats:bold> with substitutedbenzaldehydes after microwave irradiation led to1‐alkyl‐3‐aryl‐2,3‐dihydro‐1<jats:italic>H</jats:italic>‐naphth[1,2‐<jats:italic>e</jats:italic>][1,3]oxazines,which proved to be three‐component (r<jats:sup><jats:italic>t</jats:italic></jats:sup>‐o‐r<jats:sup><jats:italic>c</jats:italic></jats:sup>) tautomeric mixtures in CDCl<jats:sub>3</jats:sub> at 300 K. The electronic effects of the 1‐alkyl and 3‐aryl groups on the tautomeric ratios could be determined for both the ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and the ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria with the aid of two‐variant linear equations. A significant difference was found between the coefficients of the Meyer parameter <jats:italic>V</jats:italic><jats:sup>a</jats:sup>, which characterises the volume of the portion of the alkyl substituent within 0.3 nm of the reaction centre, for ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria, and this is explained in terms of the stereoelectronic effect caused by the alkyl substituent at position 1. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)</jats:p> |
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| author | Tóth, Diána, Szatmári, István, Fülöp, Ferenc |
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| description | <jats:title>Abstract</jats:title><jats:p>New 1‐(1‐aminoalkyl)‐2‐naphthols <jats:bold>8</jats:bold>–<jats:bold>11</jats:bold> have been synthesised by the condensation of 2‐naphthol with aliphaticaldehydes in the presence of ammonia, followed by acidic hydrolysis. The condensation of <jats:bold>7</jats:bold>–<jats:bold>11</jats:bold> with substitutedbenzaldehydes after microwave irradiation led to1‐alkyl‐3‐aryl‐2,3‐dihydro‐1<jats:italic>H</jats:italic>‐naphth[1,2‐<jats:italic>e</jats:italic>][1,3]oxazines,which proved to be three‐component (r<jats:sup><jats:italic>t</jats:italic></jats:sup>‐o‐r<jats:sup><jats:italic>c</jats:italic></jats:sup>) tautomeric mixtures in CDCl<jats:sub>3</jats:sub> at 300 K. The electronic effects of the 1‐alkyl and 3‐aryl groups on the tautomeric ratios could be determined for both the ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and the ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria with the aid of two‐variant linear equations. A significant difference was found between the coefficients of the Meyer parameter <jats:italic>V</jats:italic><jats:sup>a</jats:sup>, which characterises the volume of the portion of the alkyl substituent within 0.3 nm of the reaction centre, for ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria, and this is explained in terms of the stereoelectronic effect caused by the alkyl substituent at position 1. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)</jats:p> |
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| imprint | Wiley, 2006 |
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| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
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| physical | 4664-4669 |
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| spelling | Tóth, Diána Szatmári, István Fülöp, Ferenc 1434-193X 1099-0690 Wiley Organic Chemistry Physical and Theoretical Chemistry http://dx.doi.org/10.1002/ejoc.200600447 <jats:title>Abstract</jats:title><jats:p>New 1‐(1‐aminoalkyl)‐2‐naphthols <jats:bold>8</jats:bold>–<jats:bold>11</jats:bold> have been synthesised by the condensation of 2‐naphthol with aliphaticaldehydes in the presence of ammonia, followed by acidic hydrolysis. The condensation of <jats:bold>7</jats:bold>–<jats:bold>11</jats:bold> with substitutedbenzaldehydes after microwave irradiation led to1‐alkyl‐3‐aryl‐2,3‐dihydro‐1<jats:italic>H</jats:italic>‐naphth[1,2‐<jats:italic>e</jats:italic>][1,3]oxazines,which proved to be three‐component (r<jats:sup><jats:italic>t</jats:italic></jats:sup>‐o‐r<jats:sup><jats:italic>c</jats:italic></jats:sup>) tautomeric mixtures in CDCl<jats:sub>3</jats:sub> at 300 K. The electronic effects of the 1‐alkyl and 3‐aryl groups on the tautomeric ratios could be determined for both the ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and the ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria with the aid of two‐variant linear equations. A significant difference was found between the coefficients of the Meyer parameter <jats:italic>V</jats:italic><jats:sup>a</jats:sup>, which characterises the volume of the portion of the alkyl substituent within 0.3 nm of the reaction centre, for ring<jats:sup><jats:italic>trans</jats:italic></jats:sup>–chain and ring<jats:sup><jats:italic>cis</jats:italic></jats:sup>–chain equilibria, and this is explained in terms of the stereoelectronic effect caused by the alkyl substituent at position 1. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)</jats:p> Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐<i>e</i>][1,3]oxazines European Journal of Organic Chemistry |
| spellingShingle | Tóth, Diána, Szatmári, István, Fülöp, Ferenc, European Journal of Organic Chemistry, Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines, Organic Chemistry, Physical and Theoretical Chemistry |
| title | Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_full | Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_fullStr | Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_full_unstemmed | Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_short | Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| title_sort | substituent effects in the ring–chain tautomerism of 1‐alkyl‐3‐arylnaphth[1,2‐<i>e</i>][1,3]oxazines |
| title_unstemmed | Substituent Effects in the Ring–Chain Tautomerism of 1‐Alkyl‐3‐arylnaphth[1,2‐e][1,3]oxazines |
| topic | Organic Chemistry, Physical and Theoretical Chemistry |
| url | http://dx.doi.org/10.1002/ejoc.200600447 |