DIRECT EVIDENCE ON THE MECHANISM OF THE OXIDATION OF 2,3-DIMETHYLINDOLE BY INORGANIC PEROXO ANIONS

被引：10

作者：

BALON, M ^{[1
]}

MUNOZ, M ^{[1
]}

GUARDADO, P ^{[1
]}

HIDALGO, J ^{[1
]}

CARMONA, C ^{[1
]}

机构：

[1] UNIV SEVILLA,FAC FARM,DEPT QUIM FIS,E-41012 SEVILLE,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 26期

关键词：

D O I：

10.1021/jo00078a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanisms of the 2,3-dimethylindole (1) oxidation to 3-methylindole-2-carbaldehyde (3) by peroxodisulfate and peroxomonosulfate anions have been investigated in H2SO4/20 % v/v methanol-water solutions. Because indolenines have been postulated as intermediates in the oxidation of some indole derivatives, we have also analyzed the reactivity of 3-hydroxy-2,3-dimethyl-3H-indole (2a) with both peroxo anions. From these and previous studies, it is concluded that the reactions proceed in three steps: electrophilic attack of the peroxidic bond at the C-3 atom of indole to form the indolenine intermediate, a second peroxo anion attack on the enamine tautomer of this intermediate followed by hydrolysis to give 3-methylindole-2-carbaldehyde (3).

引用

页码：7469 / 7473

页数：5

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