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Synthesis of Five- and Six-Membered-Ring Compounds by Environmentally Friendly Radical Cyclizations Using Kolbe Electrolysis

Frédéric Lebreux, Ferdinando Buzzo, István E. Markó*

*Département de Chimie, Université catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium, Email: istvan.markouclouvain.be

F. Lebreux, F. Buzzo, I. E. Markó, Synlett, 2008, 2815-2820.

DOI: 10.1055/s-0028-1083547 (free Supporting Information)


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Abstract

Substituted carbocycles, tetrahydrofurans, and tetrahydropyrans can be efficiently obtained from unsaturated carboxylic acids. The methodology involves a Kolbe decarboxylation followed by an intramolecular radical cyclization and a radical­radical cross-coupling process.

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proposed Kolbe decarboxylation-radical cyclization-radical capture



Key Words

Kolbe Electrolysis, cyclopentanones, tetrahydrofurans, cyclization, electron transfer, green chemistry, heterocycles, radical reactions, electrochemistry


ID: J60-Y2008-3450