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http://dx.doi.org/10.18419/opus-1142
| Autor(en): | Effenberger, Franz Roos, Michael Ahmad, Roshan Krebs, Andreas |
| Titel: | Carbodesilylierung von (Trimethylsilyl)imidazolen und -pyrazolen |
| Sonstige Titel: | Carbodesilylation of (trimethylsilyl)imidazoles and -pyrazoles |
| Erscheinungsdatum: | 1991 |
| Dokumentart: | Zeitschriftenartikel |
| Erschienen in: | Chemische Berichte 124 (1991), S. 1639-1650. URL http://dx.doi.org./10.1002/cber.19911240727 |
| URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-43946 http://elib.uni-stuttgart.de/handle/11682/1159 http://dx.doi.org/10.18419/opus-1142 |
| Zusammenfassung: | The preparation of the 1-methyl(trimethylsilyl) (TMS)-substituted imidazoles 3a, 4a, 8, 9, and 11a by silylation of the corresponding metallated imidazoles is described. Carbodesilylation of 3 with aldehydes or carboxylic halogenides occurs selectively in 2-position. In the presence of a strong base (CsF) the reactivity against carbon electrophiles correlates well with the stability of the imidazolyl anions; regioselective carbodesilylation in 2-, 5-, or 4-position of the twofold TMS-substituted imidazoles 3a and 9 therefore is possible, which allows the synthesis of a great variety of hydroxyalkyl-substituted imidazoles and of acylimidazoles. By using the dimethylsulfamoyl substituent as an N-protecting group, the N- unsubstituted 5-benzoylimidazole (26) as well as the comparable 5-benzoyl-pyrazole (30b) and 5-(hydroxyphenylmethyl)-pyrazole (30a) are accessible. |
| Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
| Datei | Beschreibung | Größe | Format | |
|---|---|---|---|---|
| eff213.pdf | 1,3 MB | Adobe PDF | Öffnen/Anzeigen |
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