Darstellung und Umwandlung von 1-Hydroxyindolin-2-onen

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The photolytical behaviour of 2-(4-tert-butyl-2-nitrophenyl)-2-methylpropanoic acid has been investigated. While its crystals are photostable due to unfavourable conformational parameters in the solid state, irradiation in methanol gives a 1-hydroxyindolin-2-one and a hydroxylamine in an unspecific reaction. Photolysis of the sodium carboxylate rapidly leads to decomposition products, indicating a change in reaction mechanism. The (-)-menthyl ester shows the typical photochemical behavior of o-tert-butylnitrobenzenes. The (-)-menthyl group as chiral auxiliary did not lead to any diastereomeric exess in the main photoproduct. 2-(4-tert-Butyl-2-nitrosophenyl)-2-methylpropanoic acid did not act as a classical nitroso spin trap for various radicals. With 2-cyano-2-propyl radicals, however, addition of two radicals is observed with formation of an N-oxide. Surprisingly, an analogous product is found even with the highly hindered 2-(3,5-di-tert-butyl-2-nitrosophenyl)-2-methylpropanoic acid. Although postulated as intermediate, a nitroxide, being the expected product of spin trapping, could not be isolated in either case.
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Dokumententyp:
Wissenschaftliche Abschlussarbeiten » Dissertation
Fakultät / Institut:
Fakultät für Chemie
Dewey Dezimal-Klassifikation:
500 Naturwissenschaften und Mathematik » 540 Chemie
Stichwörter:
spin adducts, spin trapping, radical chemistry, photochemistry, ortho-alkylnitrobenzenes, nitroxides, N-oxides, 1-hydroxyindolin-2-ones, chiral hydroxamic acids
Beitragende:
Prof. Dr. Döpp, Dietrich [Betreuer(in), Doktorvater]
Prof. Dr. rer. nat. Veeman, Wiebren S. [Gutachter(in), Rezensent(in)]
Sprache:
Deutsch
Kollektion / Status:
Dissertationen / Dokument veröffentlicht
Datum der Promotion:
22.09.2005
Dokument erstellt am:
22.09.2005
Dateien geändert am:
24.10.2006
Medientyp:
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