|Title||Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds|
|Publication Type||Journal Article|
|Year of Publication||2013|
|Authors||Casey BM, Sadasivam DV, Flowers, II RA|
|Journal||Beilstein Journal of Organic Chemistry|
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.