Dp. Curran et Ht. Liu, RADICAL TRANSLOCATION REACTIONS ACROSS AMIDES - 1,5-HYDROGEN-TRANSFERREACTIONS OF O-IODOBENZAMIDES AND N-(O-IODOBENZYL) AMIDES, Journal of the Chemical Society. Perkin transactions. I, (11), 1994, pp. 1377-1393
Radicals derived from N,N-disubstituted o-iodobenzamides undergo rapid
1.5-hydrogen-transfer reactions. The regioselectivity of these reacti
ons 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.