PM3 semi-empirical study of stereoelectronic effects in the Baeyer-Villiger reaction

被引：16
|
作者：
Hannachi, H
Anoune, N
Arnaud, C
Lanteri, P
Longeray, R
Chermette, H
机构：
[1] Univ Lyon 1, Lab Chim Phys Theor, F-69622 Villeurbanne, France
[2] Univ Lyon 1, CPE, Lab Chimiometrie & Synth Organ, F-69622 Villeurbanne, France
[3] Inst Rech Catalyse, UPR 7401, F-69626 Villeurbanne, France
来源：
THEOCHEM-JOURNAL OF MOLECULAR STRUCTURE | 1998年 / 434卷
关键词：
Baeyer-Villiger reaction; PM3; bond order; reaction coordinate;
D O I：
10.1016/S0166-1280(98)00096-7
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The Baeyer-Villiger reaction of polymethoxybenzaldehydes with peroxysuccinic acid (PSA) is studied theoretically. The semi-empirical SCF-MO/PM3 method has been used to study the reaction and to calculate the energy profiles. In addition, heat of formation computations and bond order analyses of the transition species along the reaction coordinates have been performed and are interpreted qualitatively in terms of electron flow through the system during aryl migration. Our results support the hypothesis that the second step is a concerted reaction. Our data support a definite effect of the substituent on the aryl migration. The theoretical predictions are in good agreement with experimental results. (C) 1998 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：183 / 191
页数：9
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