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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.
Curran et al. (Sat,) studied this question.