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http://dx.doi.org/10.18419/opus-1111
Autor(en): | Effenberger, Franz Mack, Karl-Ernst Niess, Rolf Reisinger, Friedrich Steinbach, Adalbert Stohrer, Wolf-Dieter Stezowski, John J. Rommel, Ilse Maier, Andreas |
Titel: | Dimeric σ-complexes : intermediates in the oxidative dimerization of aromatics (Aminobenzenes ; 19) |
Erscheinungsdatum: | 1988 |
Dokumentart: | Zeitschriftenartikel |
Erschienen in: | Journal of Organic Chemistry 53 (1988), S. 4379-4386. URL http://dx.doi.org./10.1021/jo00253a035 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-43544 http://elib.uni-stuttgart.de/handle/11682/1128 http://dx.doi.org/10.18419/opus-1111 |
Zusammenfassung: | Dimeric σ-complexes 2, postulated intermediates in the oxidative dimerization of aromatics, were obtained by oxidation of tripprolidin-1-ylbenzenes 1a-f with silver nitrate. Treatment of 2 with strong base gave biphenyls 4. In solution, especially under the influence of light, compounds 2 dissociate to radical cations 1o+,which react irreversibly with solvent under H abstraction to give σ-complexes 3. Crystal structures were determined by X-ray diffraction methods for compounds 2a and 2c. Reactions of triaminobenzenes 8 and 9 with bromine and halocyanogens gave mixtures of substitution (10/ 11) and dimerization products (12/ 13). This product formation can be plausibly explained in terms of known steric and electronic factors of both reaction partners. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
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