Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds

…, DV Sadasivam, RA Flowers II

Index: Casey, Brian M.; Sadasivam, Dhandapani V.; Flowers II, Robert A. Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1472 - 1479

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Abstract

Abstract The synthesis of 2-tetralones through the cyclization of δ-aryl-β-dicarbonyl substrates by using CAN is described. Appropriately functionalized aromatic substrates undergo intramolecular cyclizations generating 2-tetralone derivatives in moderate to good yields. DFT computational studies indicate that successful formation of 2-tetralones from δ- aryl-β-dicarbonyl radicals is dependent on the stability of the subsequent cyclohexadienyl ...