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Darstellung und Reaktionen von 1,3,5-Tris(dialkylamino)-2-nitrosobenzolen (Aminobenzole ; 9)
| Content Provider | Semantic Scholar |
|---|---|
| Author | Effenberger, Franz Kurtz, Walter Fischer, Peter |
| Copyright Year | 1974 |
| Abstract | Die Triaminobenzole 2 reagieren mit Distickstofftetroxid (N2O4) zu den Nitrosoverbindungen 4, wahrend selbst so reaktive Aromaten wie N,N-Dimethylanilin mit N2O4 nitriert werden. Diese Divergenz in der Produktbildung last sich uber die unterschiedlichen Nucleophilie der Aromaten und die verschiedenen Dissoziationsmoglichkeiten des N2O4 deuten. Die Verbindungen 4 und 7 werden ausschlieslich am Nitrososauerstoff alkyliert und protoniert; die UV-und 1H-NMR-Spektren der dabei gebildeten Chinoniumsatze 9, 10 werden diskutiert und gedeutet. Uber Pd/Aktivkohle lassen sich die Nitrosobenzole 4 zu den entsprechenden Anilinen 14 hydrieren. Eine praparative brauchbare Diazotierung dieser Amine gelingt nicht, dagegen reagieren die 4-Nitroso-N,N-dialkylaniline 15 mit NO in guten Ausbeuten zu den bemerkenswert stabilen Diazonium-nitraten 16. The triaminobenzenes 2 react with dinitrogen tetroxide (N2O4) to yield the nitroso compounds 4 while even arenes as reactive as N, N- dimethylaniline are nitrated by N2H4. This discrepancy in the product formation can be rationalized in terms of increasing nucleophilic potential of the aromatic substrates and in terms of different dissociation pathways of the N2O4. This discrepancy in the product formation can be rationalized in terms of increasing nucleophilic potential of the aromatic substrates and in terms of different dissociation pathyways of the N2O4 moiety. Alkylation and protonation of compounds 4and 7 takes place exclusively at the nitroso oxygen; the u.v. and 1H n.m.r. spectra of the quinone imonium salts 9, 10thus formed are analyzed and discussed. Reduction of the nitrosobenzenes 4with a Pd/C catalyst affords the anilines 14. Diazotation of these amines was not successful on a preparative scale whereas the 4-nitroso-N,N-dialkylanilines 15 react with NO to form the remarkably stable diazonium salts 16 in good yield. |
| File Format | PDF HTM / HTML |
| DOI | 10.18419/opus-1022 |
| Alternate Webpage(s) | http://elib.uni-stuttgart.de/bitstream/11682/1039/1/eff96.pdf |
| Alternate Webpage(s) | https://doi.org/10.18419/opus-1022 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
