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The Intramolecular Radical Cation Induced Diels-Alder Reaction in the Diene - Diene Format

Author(s): David B. Rusterholz | David B. Gorman | Paul G. Gassman

Journal: Molecules
ISSN 1420-3049

Volume: 2;
Issue: 5;
Start page: 80;
Date: 1997;
Original page

Keywords: Radical cation | Diels-Alder reaction | intramolecular cyclization

Two 1,3,8,10-undecatetraenes were synthesized to test the viability of the intramolecular radical cation induced Diels-Alder reaction in the diene - diene format. Cyclization was successful only for the substituted tetraene with the lower oxidation potential. The major hexahydroindene product possessed a trans ring juncture demonstrating a selectivity for the endo stereochemistry.
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