Experimental and theoretical study of the reactivity of primary and secondary enaminones toward diphenylketene. A comparison of AM1 and HAM/3 semiempirical …

…, Y Takahata, C Kascheres

Index: Eberlin, Marcos N.; Takahata, Yuji; Kascheres, Concetta Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5150 - 5155

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Citation Number: 18

Abstract

Diazodiphenylethanone (1) reacts with acyclic enamino ketones 2 and enamino esters 3 to form products of electrophilic attack of diphenylketene at C,(5) and nitrogen (6 and 7). 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 4, which, by HAM/3, show a ...