Interplay of ortho-with spiro-cyclisation during iminyl radical closures onto arenes and heteroarenes

RT McBurney, JC Walton

Index: McBurney, Roy T.; Walton, John C. Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1083 - 1092

Full Text: HTML

Citation Number: 8

Abstract

Abstract Sensitised photolyses of ethoxycarbonyl oximes of aromatic and heteroaromatic ketones yielded iminyl radicals, which were characterised by EPR spectroscopy. Iminyls with suitably placed arene or heteroarene acceptors underwent cyclisations yielding phenanthridine-type products from ortho-additions. For benzofuran and benzothiophene acceptors, spiro-cyclisation predominated at low temperatures, but thermodynamic control ...