Radical translocation reactions across amides. 1,5-Hydrogen-transfer reactions of o-iodobenzamides and N-(o-iodobenzyl) amides

Radicals derived from N,N-disubstituted o-iodobenzamides undergo rapid 1,5-hydrogen-transfer reactions. The regioselectivity of these reactions is coupled to the rotamer population of the starting iodobenzamide, and the products vary with changing amide substituents. Related 1,5-hydrogen-transfer reactions are observed for N-alkyl-N-(o-iodobenzyl)-benzamides and -acetamides.