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

Autor: Brian M. Casey, Dhandapani V. Sadasivam, Robert A. Flowers II
Jazyk: angličtina
Rok vydání: 2013
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 9, Iss 1, Pp 1472-1479 (2013)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.9.167
Popis: 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 radical intermediates. Furthermore, DFT computational studies were used to rationalize the observed site selectivity in the 2-tetralone products.
Databáze: Directory of Open Access Journals