On the mechanism of the dimethyldioxirane oxidation of σH adducts (Meisenheimer complexes) generated from nitroarenes and carbanions

被引：29

作者：

Adam, W

Makosza, M

Zhao, CG

Surowiec, M

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 04期

关键词：

D O I：

10.1021/jo9915628

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the novel dimethyldioxirane (DMD) oxidation of sigma(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions was elucidated. The proposed mechanism, which is akin to that of the oxidative Nef reaction, is supported by the isolation of the cyclohexadienone intermediate and the lack of a primary kinetic isotopic effect. Protic solvents (H2O, MeOH) enhance the reactivity of DMD through intermolecular hydrogen bonding.

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页码：1099 / 1101

页数：3

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