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2, rt) was identified to be 6-iodomethyl-2,3,4,5- tetrahydropyridine-2-one in 37% yield via a six-membered-ring closure, which in turn indicated that the formation of 9 was not an ionic process.
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The activation energies for 1,5-H migration of radicals 22 (R = Cl) and 23 (R = Cl) were also computed (B3LYP/6-31G*) to be 9.1 and 7.5 kcal/mol, respectively, much higher than the activation energies for the preferred cyclization, in excellent agreement with the experimental results in eqs 2 and 3.
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