Radical Cation Initiated Cycloaddition Reactions Between 2-Vinylindoles and β-Substituted Enaminonitriles

Autor:	Eberhard Steckhan, Siegfried Blechert, Christoph Gürtler
Rok vydání:	2006
Předmět:	Reaction mechanism Diene Chemistry Reaction step Radical Organic Chemistry General Chemistry Ring (chemistry) Photochemistry Medicinal chemistry Catalysis Cycloaddition Cyclopropane chemistry.chemical_compound Radical ion
Zdroj:	Chemistry - A European Journal. 3:447-452
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.19970030317
Popis:	Electron transfer initiated cycloaddition reactions between 2-vinylindoles, acting as heterodienes, and β-substituted enaminonitriles lead to different cycloaddition products depending on the substituents. Initiated by potentiostatically controlled electrolysis, an anellation of a cyclopropanated five-membered ring system to the diene yielding cyclopropapyrrolo[1,2-a]indoles can be achieved in just one reaction step. Interestingly, the formation of a cyclopropane ring system takes place in reaction mechanisms which involve radicals and radical cations. In addition to these products, [4 + 2]-cycloaddition products with subsequent [1,4] dialkylamino shifts can also be formed. The formation of both products can be attributed to new reaction pathways via radical cation intermediates.
Databáze:	OpenAIRE
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