Abstract
Diazodiphenylethanone reacts with acyclic enamino ketones and enamino esters to form products of electrophilic attack of diphenylketene at C α and nitrogen. The relative reactivity of the different enaminones was shown to be consistent with HOMO energies determined by the HAM/3 semiempirical method. However, this approach could not completely explain the reactivity of the cyclic enamino ketones, which, by HAM/3, show a high-energy second HOMO corresponding to the nonbonded pair of electrons on oxygen
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