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

TitleMechanistic studies on the CAN-​mediated intramolecular cyclization of δ-​aryl-​β-​dicarbonyl compounds
Publication TypeJournal Article
Year of Publication2013
AuthorsCasey BM, Sadasivam DV, Flowers, II RA
JournalBeilstein Journal of Organic Chemistry
Volume9
Start Page1472
Pagination8
Abstract

The synthesis of 2-​tetralones through the cyclization of δ-​aryl-​β-​dicarbonyl substrates by using CAN (cerium(IV) ammonium nitrate) is described. Appropriately functionalized arom. substrates undergo intramol. cyclizations generating 2-​tetralone derivs. 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 radical intermediates. Furthermore, DFT computational studies were used to rationalize the obsd. site selectivity in the 2-​tetralone products.