Lithium N-butyl-4-pentenylamide (k) ln tetrahydrofuran at 22 'C rearranged smoothly to give a mixture (after protonatlon) of 1-butyl-Z-methylpyrrolldlne, formed by an unusual cyclization process, and cls-and trans-N-butyl-3-pentenylamine, in the presence of 2 0 molar equiv of hexam?i%ylphosphoramlde, the total rate of isomenzation was accelerated by a factor of 2 5 The potential utility of small ring lithium dlalkylamldes to serve as mechanistic probe< for electron transfer processes in reactions of llthlum dlalkylamldes and the rearrangements of these species were discussed in the accompanying communication In this communication we present the results of our preliminary studies of lithium N-butyl-4-pentenylamlde (i), a representative member of another class of potential mechanistic probes for such electron transfer processes Species such as k could undergo the sequence of reactions shown in eq 1 to give, ultimately, cycllzed products Although there is no doubt that analogous carbon-centered 5hexenyl radicals cycllze,' the cycllzatlons of 4-pentenylaminyl radicals, step two ln eq 1, 1s still questionable Cycllzatlon of the N-propyl-4-pentenylaminyl radical ($) formed upon thermolysis of the corresponding tetrazlne 3y4 has been reported as has cyclization of 2 formed by photolysls of the corresponding N-chloroamine 5 However, when 2 was prepared by the reaction of the parent amine with photochemlcally generated tert-butoxyl radicals, Maeda and Ingold saw no indication of cyclization in EPR studies at low temperatures, 6 but recent results suggest that there may have been experimental problems in these studies 7 On balance, we felt that the potential for aminyl radical cycllzatlon warranted a study of the lithium amide k