EXPERIMENTAL AND THEORETICAL-STUDY OF THE REACTIVITY OF PRIMARY AND SECONDARY ENAMINONES TOWARD DIPHENYLKETENE - A COMPARISON OF AM1 AND HAM/3 SEMIEMPIRICAL METHODS

被引：17

作者：

EBERLIN, MN ^{[1
]}

TAKAHATA, Y ^{[1
]}

KASCHERES, C ^{[1
]}

机构：

[1] UNIV ESTADUAL CAMPINAS,INST QUIM,CP 6154,BR-13081 CAMPINAS,SP,BRAZIL

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 17期

关键词：

D O I：

10.1021/jo00304a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diazodiphenylethanone (1) reacts with acyclic enamino ketones 2 and enamino esters 3 to form products of electrophilic attack of diphenylketene at Ca (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 high-energy second HOMO corresponding to the nonbonded pair of electrons on oxygen. © 1990, American Chemical Society. All rights reserved.

引用

页码：5150 / 5155

页数：6

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