Substituent effects in the ring-chain tautomerism of 1-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines
The condensation of Betti base analog aminonaphthols with substituted benzaldehydes or aliph. aldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines (16-22) and 3-alkyl-1-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (23-29), which proved to be three-component (r1-o-r2, 16-22) or two-...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2003
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| Sorozat: | ANNALS OF WEST UNIVERSITY OF TIMISOARA-SERIES CHEMISTRY
12 No. 3 |
| Tárgyszavak: | |
| mtmt: | 3258704 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/30979 |
| Tartalmi kivonat: | The condensation of Betti base analog aminonaphthols with substituted benzaldehydes or aliph. aldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines (16-22) and 3-alkyl-1-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (23-29), which proved to be three-component (r1-o-r2, 16-22) or two-component (r1-r2, 23-29) tautomeric mixts. in CDCl3 at 300 K. The electronic effects of the 3-aryl or 3-alkyl groups on the tautomeric ratios could be described by the equation log KX = ρσ+ + log KX=H (16-22) and log KR = 7.88Va + 0.55 (23-29) resp. Study of the influence of aryl substituents at position 1 indicated that in the trans form a stereoelectronic effect is present; this was supported by dual substituent parameter treatment of the 13C chem. shift changes induced by Ph substituents. [on SciFinder(R)] |
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| Terjedelem/Fizikai jellemzők: | 175-182 |
| ISSN: | 1224-9513 |